Four Letter Words and How We Use Them
by SomethingSomethingNothing
Summary: AU Lit. Jess raked a hand in his dark hair, annoyed he had even given a moment's notice to this girl. It wasn't his business to interrupt Tristan's horrible attempts at seduction. So she had one obscure book in her bag. Whatever. It was a fluke.
1. Chapter 1

AU. I love the idea of Jess at Chilton and I had something I wanted to play with.

Story: Jess finds himself - reluctantly - intrigued by transfer student Rory. As he gets to know her, he realizes her intelligence and wit, making it difficult to ignore his intrigue any longer.

* * *

"Rory?"

"Y-yes," she stammered, nodding at the teacher after he pronounced her nickname correctly. She was obviously nervous as she stood in front of a class of sixty pairs of eyes boring into her. Jess Mariano, watching from afar, couldn't blame her; he wasn't one for that much attention himself.

Mr. Medina cleared his throat as he flitted his attention up to his students. "Alright class, this is Rory Gilmore, a new student who just transferred in from Stars Hollow High. Please be courteous to her in the days approaching while she adjusts to Chilton."

The new girl forced herself to move toward the back of the room, where the only empty seat was available. Jess noticed her and disregarded her in the same breath. As soon as he did, he glanced back in her direction, noticing a book hanging out of her bag. He could only glance a few words of the title but he was sure he had it right. It was too rare for another person to know that book if it weren't assigned to them. That intrigued him enough to give her another notice.

He forced himself to take a breath – failing to notice he had stopped after noticing her book - as she took the empty seat in front of him. He gave a hard stare at the back of her head, a mix of deep brown and auburn strands flowing neatly down her back. He huffed, hating whatever was swirling inside him at this first impression of a _maybe_ book-smart girl who had enough charisma to grab his attention without even saying anything.

There was no need to glance to his left. Tristan DuGrey was making it more than clear he was interested in this girl. Subtly was never his strong suit, especially with women. Jess gave a noncommittal look over to see what the trust-fund snob was thinking. That second alone told him everything.

Tristan was a wolf in sheep's clothing in that brief second. The lust, the _desire_ was apparent on his face. His eyes gleamed and his fingers twitched with longing to reach out to his new-found "Virgin Mary". He had a habit of calling all girls of similar innocent appearance that name - "Mary" - and Jess didn't doubt it would be chosen for this _Rory_ as well.

Jess had no reason to bother himself with this. He had a scholarship to keep.

What was _that_ book of all books doing in her bag?

There was something more here.

Tristan reached out to his right and tugged on the zipper of the girl's backpack. A plethora of books, pencils, and index cards spilled out, littering the tiled floor. They were far back enough in the crowded room that barely anything would be noticed from the front. Rory looked not once, but twice, before bending forward to collect her things. If she was annoyed or upset, her soft face didn't give it away.

Tristan grinned to himself and snaked out an arm to snatch her. He pulled the waif of a girl toward him until she landed in his lap. Mr. Medina was still very focused on the blackboard, not bending his head back once.

Tristan weaseled his arm around her waist and gave her his best smoldering charm. "Hey, there, Mary," he cooed. "Need anyone to show you around school? I know some places that are off limits."

She didn't seem impressed with him at all. Jess smirked to himself as he caught Tristan's shock at this new girl's lack of swooning over him. _Definitely a first_ , Jess thought. _Most girls would be wet by now._

"My name is _Rory_ , not Mary," she frowned, eyes narrowing. She started to open her mouth and say more, already raising up her hands to push away from Tristan. Tristan grinned and started to open his own mouth, closing in on her.

Jess felt a growl in his throat. He leaned over and snatched Rory away from the snake. The movement wasn't planned and before he knew it she was in his _own_ lap, inches from his face. Neither of them moved as they watched each other for a long second. Her piercing, icy eyes searched his and he felt himself tense up, realizing she was finding something in them. More than he certainly _wanted_ her to see. His breath caught in his throat before he gave her a light shove.

"Move," was all he said.

She got up, returning to the seat in front of her. Tristan gave a small snicker, reading the situation as jealousy on Jess's part. The blonde boy went back to leaning over to talk with his friends, like he had been before "Mary" had peaked his interest.

Jess raked a hand in his dark hair, annoyed he had even given a moment's notice to this girl. It wasn't his business to interrupt Tristan's horrible attempts at seduction. So she had one obscure book in her bag. Whatever. It was a fluke.

He rolled his eyes and began taking notes on what Mr. Medina was saying. His pencil barely scraped the paper when something bounced into his line of vision. He blinked for a moment, before snatching and unfolding the paper.

"Thank you," it said, in beautiful, clean script.

Jess felt his heart fly up to his throat, immediately hating the reaction. He bit hard on the inside of his cheek. Hastily, he scribbled something back and tossed it forward to her.

Rory carefully unfolded the paper ball and felt a smile on her lips. There was a brief moment of surprise she had caught in the brooding eyes of her "rescuer" when she landed in his lap. As quickly as she had recognized it, he had his mask of indifference back up. But the second she saw of his softened features she knew was a second more than anyone else had seen.

The note now unfolded, she read the instructions: "Turn around." As she did, the tips of her hair fluttering with her, she was met with a paper football square in the face.

And from that moment, she decided there was something more to Jess, something she had seen briefly, but would try to see again.


	2. Chapter 2

A/N: If you read the first chapter, I updated a few things. I got incredibly inspired this week - it's my first time writing in years - and if you want to make sure the flow stays consistent, now is a good time.

I love Rory and Jess together. I personally relate to Jess a ton, so I find writing for him not too much of a stretch.

I had the first test chapter up one day and I felt really encouraged even off six reviews to keep going, so I hope everyone enjoys where I take this. =^..^=

* * *

As soon as his final class released, Jess grabbed his bag and bolted for the door. There really was no reason to be in a rush. His parents were gone – he didn't really care where they were this time. It was more awkward when they _were_ around at this point. Coming home to an empty house, free to do as he pleased, had been a way of life since even elementary school. Kids in his class had been jealous and floored when it became common knowledge. Jess always assumed that it was normal to be left alone a lot and now that he was older, he preferred it.

He hadn't see Rory – that girl from his English class with that obscure book - in any more of his classes the rest of the day, but that was no surprise. Chilton was a large school, practically a college campus in size. Chances of them having several classes in common were slim.

It wasn't until he was darting across the courtyard, making his way to the parking lot, that he saw her again. She suddenly appeared at his side, matching his quick walking pace. She gave him a small smile and gentle wave. His breath caught in his throat as the sun made her hair glimmer, playing out the hues of red and caramel and giving them a golden glow. Quickly, he went back to looking in front of him. He just wanted to get home and be alone.

"You know, typically when someone thanks someone else, that someone else says 'your welcome' or 'my pleasure' or some variance of those phrases," she remarked playfully.

He couldn't help but be a bit transfixed by her conversation attempt. He went for his usual dryness. "Really? I'll jot that down to remember for next time."

Rory raise an eyebrow slowly, her pink lips curling up. "Next time, huh? You plan on protecting me often?"

His face reddened as his mouth quickly worked into a scowl. He accelerated his pace, trying to get to the parking lot as fast as he could. _This_ _i_ _s_ _embarrassing,_ he thought. He didn't know how to react to whatever she was trying to do. _Is this supposed to be small talk? Certainly not impressive._ He cursed to himself silently, wondering why he had even humored the conversation at first.

"Now I'll have you know," she continued, appearing again by his side and now slightly out of breath yet persistently trying her hardest to match his speed, "I don't make a habit out of being a damsel in distress. In fact, if you'd have given me one more minute I would've been able to resolve the situation myself."

Jess gave her an incredulous look, clearly not believing her. "Oh yeah? How's that? Tristan looked like he was getting _awfully_ fresh from where I was sitting."

Rory rolled her eyes and huffed, dismissing his comment. "Well, anyway, the point is… thanks." she smiled, tucking a strand of loose, straight hair away from her face. "That guy must be used to girls melting at his touch instantly I assume."

He grunted. "You could say that."

She shook her head. "Guys like that are awful. I don't get it."

"Huh."

He really wasn't sure what to say, but so far he was realizing she was smarter than he may have first given her credit for. Without realizing, he slowed down his pace so she wouldn't be stumbling to keep up with him. Her cheeks were flushed and he couldn't stand the way noticing that was making his heart pound.

She gazed over at him, clutching her books tightly to her chest. "You don't speak much, do you?" she murmured.

Jess shrugged. "Not much to say."

He made the mistake of glancing over and saw the flash of words that had grabbed his attention earlier that day. The small book was nestled between her chest and a larger textbook, cradled delicately in her arms. _That damn book again_ , he thought in annoyance.

"That book," he heard himself ask impatiently, then paused, unsure how to continue.

Rory looked down, and pulled out the small book. "This one?"

He nodded. "Yeah. How do you know it?"

Her eyes practically glowed. "Oh, there's a bookshop just outside my town with lots of obscure stuff," she explained, "The owner is practically like a grandfather to me with how much time I've spent there over the years. He always recommends odd things he's read or come across. Do you read?"

He expected the question, but didn't want to talk about himself.

"Not much."

She narrowed her eyes and smirked. He wasn't used to other people being the ones smirking at him. "You're lying." It was a declaration, and she was sure of its truth. "You obviously know this book and anyone who knows this book has to be _somewhat_ of a bibliophile. So how do _you_ know it?"

Her blue eyes were intense and prodding as she stared him down, waiting for a proper response. He surprised himself when he started speaking almost immediately.

"My next door neighbor when I was growing up, was kind of like your store owner." He shook his head in disbelief that he was answering her, but the words kept coming. "Name was Nathan. Started giving me books when I was seven - books with words most kids my age probably wouldn't know." He felt a small smile cross his face as he thought of his old friend. "He passed away and left me his library. Didn't have any kids and seemed to think I was the closest he had to one."

"That's amazing," she said is a soft voice, seeming to understand she had been given a rare privilege. She then wrinkled up her nose at him and gave a playful shove against his shoulder. "And to think you tried to say you don't read much."

He couldn't help but look back at her and give an authentic smile. "Well," he said carelessly, the smile remaining, "What _is_ much?"

By now they were finally at his car, and Rory seemed to realize she had been following him for awhile. They both stopped and awkwardly faced each other. "I better go," she said, a bit sad. At least, he hoped she was a bit sad. He couldn't deny a part of him had been starting to enjoy their little chat.

"I can't miss my bus," she continued, "But, um… thanks. Again."

He looked into her eyes seriously for a moment. "You're welcome."

She started to turn away, and then suddenly spun back. He felt the same surprise come to his face that she had brought up in him earlier that day and quickly tried to hide it. The shine in her stunning expression showed she noticed, but wasn't going to acknowledge it.

"I just realized I still don't know your name," she pointed out.

" _We know who we are, so we don't need names_ ," Jess quoted with a smirk.

Rory shook her head and giggled softly. "Alright then." She turned and walked away, but before she got too far, he called out to her.

"It's Jess."

He felt any 'cool' points were gone. Any mystery vanished. But he felt his heart jump a bit that this girl – this girl with the obscure book, the girl that he still wasn't sure about – seemed to want to to get to know him.

"Jess," she breathed, letting the name leave her mouth slowly, before spinning back around and breaking into a light jog toward the bus stop. He repeated in his mind the breathy way she said his name the whole drive home.


	3. Chapter 3

A/N: back to back uploads since I went on a writing binge. I appreciate any comments. I really used to love wring so this is big for me and a help to see if I still have it.

Literati to come, a slow build up, but man, I love them together so much. Trust me. It's coming.

* * *

He was barely inside his room when the button-down and tie came off and were quickly replaced with a black band shirt. As first he crumpled up the uniform shirt and tie that had been offending him most of the day, preparing to toss it across the room, but he stopped. Grabbing a wire hanger, he smoothed the shirt back out and hung it up with care, draping the tie loosely around the hook.

It was still a mystery to him that Chilton had given him such a great scholarship. He knew he was smart and well-read, but most people didn't take the time to notice that for themselves. But the next door neighbor who had aroused his love of literature had seen it and made a point to get Jess the proper interviews a few years before.

Chilton was not a place he fit into socially. Academically he was top in his grade, but he didn't come from money like the rest of the students. _Like I want to be best pals with any of those yuppies anyway,_ he thought. Most of them could barely string together an original thought and would only end up at Harvard or Yale because of their connections and trust funds. Rory was probably one of the first real meaningful conversations he had had since his neighbor had passed, and that was saying something as she and him had only briefly discussed a passion for books. Still, the fact she had a book Nathan had loved gave promise that she may be a continued source of spirited conversation.

He strolled over to his CD player and hit the play button. The Pixies surrounded him instantly as he flopped on his bed, pulling out his current reading choice from his pocket. He grabbed a pencil from his bedside table and started scratching little notes along the text of his book as he read.

* * *

He didn't have English the next day but was happy to notice he shared a lunch hour with Rory. It went unnoticed yesterday because he hadn't been trying to look for her. Now he was.

Jess weaved past other students, making his way to the table where she sat alone, headphones on and a book in one hand, a sandwich in the other. He caught himself grinning to see they shared a mixed media hobby. Most people found music and reading to be distracting or overwhelming, but he felt the right music paired to the right book could only heighten both experiences. He wondered if that was her reasoning too.

She glanced up at him as he took a seat across from her. A smile formed on her lips as she finished chewing her current bite of food and set the sandwich down on its wrapping. Removing her headphones, she said, "Ah, my knight in shining armor," in a mocking tone.

He rolled his dark eyes. "I seem to believe someone made a strong point yesterday about not being a damsel."

"I can still have a bodyguard and take care of myself," she challenged, a smile seemingly always on her soft face. "You're like a… backup… or a sidekick. Sidekick sounds better." Her eyes took a sweep of the space he now occupied across from her. "Where's your lunch?"

"Somewhere else," he said dismissively. He didn't come over here for that, he had a purpose and didn't want to get sidetracked. _Keep the subject on topic, then leave,_ he reminded himself.

It was too late. She shook her head and grabbed a plastic knife, cutting her sandwich in half. Scooping up a portion, Rory stuck it out at him. "Here," she said, "It's turkey and swiss."

"I'm not taking your sandwich," he started, but the expression on her face told him he was already losing. It was a face that refused to be told 'no'.

She shook her head, "I insist," she stated firmly. "I've got plenty of food here, so just agree to half this sandwich for now and in a few minutes and can start arguing over sharing or not sharing the cheese puffs and the cookies."

Awestruck at her visibly growing impatience, he chuckled and accepted the sandwich. "Thanks," he said awkwardly, curling his fingers around it. He usually hung around in the library during lunch and had been hoping to talk with her quickly so he could run back to it. It he humored her eating this sandwich, maybe there would still be a bit of time left for him to hide off in a corner and read.

Rory beamed, her remaining half of sandwich back in her slim fingers. "No problem. I don't think I can return the favor of saving you from cocky boys," she winked, "but I can give you somewhat of a proper meal."

"Oh, so if I'm in danger of being flirted with, I'm on my own," he said in mock hurt, clutching a hand to his heart. "I see how it is."

Before she could get him sidetracked again, Jess pulled out the book he had been reading last night out of his back pocket and slid it across the table to her. Avoiding her gaze, he mumbled, "Here." He quickly took a bite of sandwich to keep himself occupied as Rory gingerly picked up the book and inspected the title and back cover.

He watched as her interest peaked on her face as she read the summary. "This sounds incredible!" she gushed, starting to flip through the pages. Her eyes seemed to catch something. "You write notes inside your books?"

"This is another book Nathan showed me," he began, ignoring her question. "It's got the same kind of vibe as the one you're reading now – maybe a bit darker - but I think you might like it."

"And the little margin notes?" she pressed.

He scratched mindlessly at the back of his neck, looking everywhere but into her eyes. "I just like to write out particular thoughts I have while reading, or if I interpreted something in a different way."

There was something almost sinister in how delighted she was by this, by the way a smile crept across her normally doll-like features. "So, in a way, I'll be getting to crawl inside your mind," she played.

Jess scowled. He had been squirming and growing more and more embarrassed as the conversation went on, and now he wanted to be anywhere but there. His fingers reached out to take the book back so he could get up and leave the table.

"Look, I can help you find a copy without my scribbling in it if you want."

Rory pulled the book out of his reach and gave him a very serious yet soft look, letting him know she was finished teasing him. "Hey, I want to read this one," she said carefully. "You just aren't exactly a 'people person' I gather, so I'm just surprised you're letting me see this."

He was no conversation expert, but if she was willing to drop the previous teasing then he could go back to being playful. "Well, it's kind of a test," he said defiantly.

Now it was her turn to frown. "A test?"

"Yeah." He gave a careless shrug. "Yesterday could have been a fluke. You could've just been carrying that book around to look all important and well-read at your new fancy school. So," he leaned in closer, "you read this and then come have a nice picking-it-apart session with me. Then we'll see if you're this – what did you call it? - _bibliophile_ you've built yourself up to be."

She nodded, mirroring him by also leaning forward. There was a spark in her eyes. "Okay, you're on," she said challengingly. "Be prepared for the most in depth book discussion of your life, Jess."

"I fully hope that is _exactly_ what I get."

It was unbelievable. This was the most interaction he had had with any classmate. Even though he still felt embarrassed and uncomfortable talking and sharing so much about himself, it oddly wasn't as terrible as he had forced himself to believe it would be. And if this book debate ended up being what she promised, he may even have more reason to talk with her. It could slowly become more comfortable.

They had gotten sucked into conversation so promptly, it hadn't dawned on him until now they were sharing a sack lunch. The brown paper bag was flattened in front of her like a place mat, with her meal in varying plastic bags dotting across it. One quick dart of the eyes around the room found flashes of catered meals and pristine lunch boxes with personal chef-cooked delicacies. Jess and Rory were the odd ones on their own private, sack lunch toting table.

"Brown bag, huh," he murmured, focusing back on Rory.

She gave a shrug. "I'm here on scholarship," she said. "There was no way I could come here otherwise."

He perked up. "I'm on scholarship too."

That interested her. "Really? Cool!"

She opened up the plastic bag of cheese puffs and tilted them toward Jess. He could see she wasn't going to take a _no_ , just like with the sandwich, so he gave a crooked smile and grabbed a few.


	4. Chapter 4

The original plan had been to run back to the library, enjoying the remaining lunch hour in solitude. It had been a routine since starting at Chilton, specifically to stay away from all the people he knew he had nothing in common with and had no interest in getting to know. That day Jess had gone in the cafeteria for the first time with the purpose to pass along the book, offering her a chance to accept his 'test', and then leave.

After giving her the book, he didn't feel the need to run off as strongly as he had went he first sat down. So he stayed.

He certainly didn't think it was going to become a habit, skipping his hour of solitude in the library. But just this once, it hadn't been so bad. On the drive home from school, he even considered doing it again. If Rory could provide this book discussion she promised, that is.

As he drove down the road leading up to his home, Jess found himself glance over at the house Nathan had lived in. For the last year, he had purposely ignored it. His eyes would stay straight ahead as he held his breath until he was away from it. He felt his entire body grow cold as he looked at it now and his grip on the steering wheel tightened. It used to be the one escape he had; the one place he didn't mind going even though he would be giving up his valuable alone time.

Before he could stop himself, he was out of the car. His face flushed as he raced up the porch and stopped sharply in front of the screen door. Mind racing, he pulled out the spare key Nathan had given him ages ago and shakily stuck it in the lock. He didn't know why he was doing it or why the key was even still carried with his others everyday like he still needed it. The pins clicked and responded to the key, but the lock didn't turn. Jess couldn't move his wrist to unlock it. He was frozen.

Just as quickly as he had arrived at the door of the only place to ever feel like a home to him, he was back in his car refusing to look at it as he drove by.

* * *

Jess was not one to arrive early for class.

He was an academic prodigy, sure, but he strolled in right as the bell chimed every day, reluctant as ever. But today he felt there may be a reason to be early.

The classroom for English started to fill up slowly and he watched from the back of the room, slouching in his seat as student after student walked through the door. His dark eyes searched and searched, but came up wanting every time. This was puzzling to him, as Rory seemed the type to be early. They were both on scholarship and had to make efforts to keep their gracious gift, but she seemed to have more of a passion to be there. Jess was mostly there because of a promise and though he may not seem the type to others, he was very strict about keeping to his word.

She finally raced inside in a blur of auburn hair and the signature blues and grays that were the Chilton uniform. A poptart clung for dear life from her small lips as she darted her eyes around frantically. This got his attention, making Jess lean forward and squint up his eyes in curiosity.

A flash of blue eyes finally met his and he felt himself forget to breathe. _She_ had _been looking me_ , he thought, taken aback. _We have a few conversations and now she's seeking me out?_

He blushed furiously, knowing he had been seeking her out as well. Recapturing his usual indifferent demeanor, he watched as she made her way over to him. She took the seat in front of him and spun to face him without missing a beat.

Removing the poptart from her mouth, she became a fury of words. "I'm ready to discuss the book you lent me, and I can't wait another second," she gushed, eyes growing wider then ever. "If we could afford to skip classes – or if I were the kind of person to skip school in the first place – I'd drag you off right now to go talk about it! And I can't talk at lunch because I joined the school paper and I have to go to a meeting for it then." Her eyes narrowed sternly at him. "So you better wait for me after school. I am _not_ afraid to chase you around again."

Jess was dumbstruck, slowly registering her whirlwind of a speech. "You… finished the book already?" he asked in a daze. It was at least twice the size of the book she was currently reading and he only gave it to her yesterday.

"I stayed up pretty much all night," she confessed. "I started out just reading one chapter to get a feel for it. Trust me, I had no idea I would stay up until four. It's a good thing I'm kind of addicted to coffee or I'd be on the floor right now."

Her excitement was cut off as Tristan approached them and took the same seat he had the previous class, to the left of Jess. Judging by the expression on his face, he was still determined to have his "Mary".

"Mary, Mary," he purred, "Been waiting to run into you again since the other day." It seemed to register to him he had interrupted their conversation. His smile grew more devilish. "Ah, getting pretty keen on loner boy, eh? He steps in at the right moment, sweeps you off your feet, and now you're smitten with your little hero."

Jess ignored him, like he usually did. It wasn't worth taking the bait. Everyone knew Jess was on scholarship and Tristan for some reason had a habit of prodding him, trying to provoke him so he would do something irrational and lose it.

Rory glared. "Well he certainly has more interesting and educated things to say than you do."

Tristan started to respond but was interrupted by the bell. Mr. Medina waltzed in the room already starting off his lecture. Rory spun back to Jess, the sweetness returning to her face.

"So, after school. Book discussion?" she whispered.

Jess felt speechless again and gave her the only words racing in his mind. "As you wish."

* * *

"The imagery evoked in that final chapter," she breathed, tilting her head back. "I reread it three times because I just couldn't get enough of it. I don't think I've ever come across a writing style like it before."

They were in the courtyard, sitting on a bench under a massive oak tree. School had been out for twenty minutes and there seemed to be no end to the praise Rory was giving the book. Jess smirked as he listened, occasionally probing her for more of her insight and giving some of his own. He surprised himself when he start thinking how much he was enjoying this. Her cheeks flushed recalling some of the racier parts of the novel, something he had counted on. It had been a somewhat underhanded revenge for all the blushing she seemed to be making him do lately. At first, it surprised him she even mentioned those plot developments. _She's not afraid to read smut, but she sure as hell blushes like a virgin bride to talk about it openly._

"So, do I pass then?"

Her words startled him. "Huh?"

"The test. You said this book was a test to see if I was as literate as I first appeared to be."

He smirked. "Oh. Yeah, I'd say for now you pass."

Rory gasped and gave him a light smack with the book. She had pulled it out to flip open passages she wanted to read aloud to him earlier. Her voice had been melodic, cherishing each word as she said them out loud. He had gotten lost in listening, finding his attention more on her voice than the words.

"For now!" she hollered, exaspperated. "You said this would prove or disprove it! Have I or have I not been passionately raving about this book for the last half hour?"

He grinned. "You have."

"Therefore," she reasoned, "I pass. No ' _for now_ 's. I pass. End of discussion."

Jess nodded, surrendering. "Alright then. You pass. End of discussion."

She looked pleased with herself and slumped down casually on the bench. Her demeanor was so calm and relaxed. During their lunch the day before, she felt like she seemed comfortable with him, but seeing her fervor over their discussion of the book was something else entirely. She seemed at peace. He ventured this was her comfort zone, and he had been allowed into it.

Rory gave a sneaky glance his way. "I liked your notes."

He felt a lump in his throat and his face grew hot. "Yeah?"

She nodded slowly, then took a breath and faced him bravely. Every time she looked him dead-on he didn't know what to think for a moment. He lost all rationale and felt vulnerable. It annoyed him that she unnerved him so easily, but he didn't regret her gazes either.

Her icy eyes were serious, but warm. "You really pulled out some things I didn't notice at first," she continued, "And your style.. obviously it was just margins but you really… Jess, do you write ever?"

"You just read what I write," he said simply.

She shook her head. "No, like _write_ write. I think you could."

He didn't know what to say. She barely knew him and was paying him this kind of compliment? _Nathan would've gotten a kick out of her_ , he thought. _She's badgering me with the same stuff he always did. They'd be two peas in a pod prestering me together._

"Maybe," he finally said, noncommittal.

She scuffed a shoe on the pavement. "You know, I wouldn't be against reading another of your books. You know, with the margin writing inside."

He couldn't help his eyes widen for a moment. "Really?"

"Yes," she said happily. "I liked crawling in your mind."

He gave a smirk and leaned toward her. "Is that so," he murmured huskily. He decided he liked her. It wasn't fair she was making him jump around inside constantly. A bit of flirtation to make her squirm right back was warranted. _Especially to see her blush,_ he thought, growing warm.

He watched her for a reaction to his tone, but realized she had missed his obvious attempt to flirt with her. Her gaze was across the lot and she was smiling and waving. Jess let his gaze follow where hers went and he saw a tall, lanky boy watching from the main gate of the school.

"Oh, there's Dean," she said, gathering her things in a rush. "I should get going."

"Dean," Jess said with an even tone.

Rory nodded, giving a small head jerk toward the tall boy. "Yeah, my boyfriend. He was picking me up today, but I told him to come later so you and I could talk for a bit. I didn't think he'd come so soon though. I figured we'd at least have an hour."

She put a hand on Jess's shoulder and looked him in the eyes, giving him one last lingering smile. "I think you're going to help me stay sane at this place."

And she was gone.

Jess remained on the bench, watching as the couple embraced and kissed before climbing in his car and driving away. He wasn't stupid. The more Jess had realized the intelligence and charm of the girl, the more he was aware she was a catch and someone that wouldn't go unnoticed for too long. _Like it matters,_ he thought. _Who cares that she has a boyfriend? It's not like I want her bugging me to take her to dinner or something._

But he knew she wouldn't be like that. He pictured sitting beside her, reading to her, and wondered if she would like a date like that. It annoyed him to wonder about it and he tried to dismiss it.

He wondered if this _Dean_ read books. If Dean loved watching her excitement and joy as she spoke about something she liked the way that Jess had.

He wondered what they talked about.


	5. Chapter 5

Friday remained uneventful at school. Jess went through the motions of class, awaiting his weekend. He mapped out in his head a day trip he wanted to take up to Philadelphia. Mr. Medina had mentioned to him after class the day before that a new bookstore had opened there that he might find interesting. When Jess had asked what exactly was so interesting about it, the English teacher gave a mysterious smile and said, "You'll have to see."

Jess got the address from him somewhat unwillingly, but after realizing he had nothing better to do he decided it may at least make a fun day trip away from Connecticut.

That thought brought up a flash of a memory in his head of back when Nathan was alive. Jess had been fourteen at the time and well into the habit of going wherever he wanted for days on end while Liz and Jimmy were off doing the very same.

 _He had been locking up the front door of his house – more out of courtesy, there certainly was nothing worth taking inside – when Nathan had spun him around, squinting down at him._

 _Nathan had always been tall, wrinkled, and stoic. His eyebrows were dark, contrasting his well peppered hair, and his light eyes always seemed to search inside of Jess when they bore into him. The old man's face at the time had been troubled and stern._

" _Where this time?" he asked in monotone._

 _Jess had shifted the duffle bag on his shoulder, the canvas bulging with books, CDs, and occasionally an article of clothing. His dark eyes returned Nathan's expression as he stood quietly for a long minute._

" _New York," he finally answered._

 _Nathan grunted. "Big Apple."_

 _Jess snorted. "Nobody calls it that."_

" _Oh yeah? And how would you know?"_

 _The boy shrugged. "I go up there a lot."_

" _How come?"_

" _Dunno. I like it. Better than here."_

 _The old man hesitated for a moment, calculating in his head. "It's a Monday."_

" _Congratulations, you want a prize for recalling the day of the week?"_

 _Nathan rolled his eyes, well accustomed to Jess's snark, and folded his arms across his broad chest. "You skipping school again, Jess? You're too smart for that."_

 _Jess dropped the bag angrily, eyes blazing. "That's the problem, it's boring!" he snapped, throwing his arms above him for a moment. He stomped back and forth on the porch. "There's no reason to go. I'm smarter than everybody there. They hand me books I was analyzing at ten years old and expect me to find something so basic out of them it makes me ill. I turn in assignments and get scolded for not doing what was asked. They don't want_ my _take on things, they want me to regurgitate something right back at them. So there's no point in turning anything in, there's no point in going."_

 _Both stood silently as his rant came to a close. Jess was well aware this was the first time he had ever yelled at Nathan. Usually, they discussed books, argued music (he refused to acknowledge some of the old man's questionable choices), and picked apart current films. He was a kindred spirit. A friend. In some ways, a father. And Jess had just lashed out at him._

 _Feeling embarrassed and even more moody than before, Jess picked his bag up and started to leave again. "Whatever, it doesn't matter," he grumbled, trying to get past Nathan._

 _A big hand came down and rested on his shoulder. Jess cautiously looked up into Nathan's eyes, expecting to see pain or anger or something similar. Instead, he found a crooked smile on the old wrinkled face and a shine to the steel colored eyes._

" _Well then," Nathan began, "Let's look for a place that will give you a reason to go."_

After that, Nathan had called up some friends and Jess had an interview by Thursday. He was immediately accepted and transferred in. A deal had been struck between Jess and his older friend that he could not skip school anymore. He had demanded a challenge and was handed one, so he best well take advantage, Nathan had declared. He said he didn't care if Jess decided on college or not, but he certainly needed to finish high school and decide from there what to do.

True to his word, Jess hadn't skipped since. He saved the itch to go somewhere until the weekend, after homework was done. There was a long period of time after Nathan passed where Jess felt truly alone and considered forgetting the whole promise of going to school, forgoing it to travel around. Something stopped him, though. He wasn't sure if he genuinely wanted to stick it out or if he was afraid Nathan's scolding would somehow reach him from the afterlife.

The final bell rang and he was suddenly in the courtyard, rushing toward his car like he did every other day. He felt a genuine smile reach his lips as he felt the excitement for his trip swirl inside him.

"Is that an actual smile I see?" a voice gasped. "More than the signature smirk today?"

He turned and caught Rory striding along beside him, trying to keep up. He gave a small chuckle and slowed down a bit for her. "Making a habit out of following me to my car now?" he asked, cocking an eyebrow.

She rolled her eyes. "Well, I was waiting for you, but you shot right past me with a dopey grin on your face," she retorted, waving up her arms. "I had no choice."

He didn't think it was possible to smile any wider. Surely his face was close to cracking. "Waiting for me," he repeated, trying not to sound delighted by the thought.

Rory blushed furiously and busied herself digging around in her bag before shoving two books into his hands. It caught him off guard and forced him to stop dead in his tracks. The first book he recognized as the one he had let her borrow for her 'test'. The second he turned over and over, taking in the title and the brief description on the back. He was surprised it was something he hadn't read before. It was by an author he recognized, but the title was one he did not.

"I was in a rush to get going yesterday after our discussion that I accidentally took your book," she explained. Sticking a finger on top of the second book, she tapped it lightly. "This is one of mine. I want you to read it."

"Do I have to pass a test now?" he smirked.

She shrugged innocently. "Maybe."

He sandwiched his book under one arm and paged through Rory's book, charmed to see neat little writing. He looked up at her with surprise. "You wrote me notes."

"I wrote you notes," she confirmed.

He couldn't deny the swelling warmth in his chest. Nathan had been the only other person to get his margin writing and would give him books with some of the old man's own thoughts penciled inside. Jess found himself speechless that Rory was admiring it enough to try it out for herself.

"So now I get to crawl inside your head," he ventured.

The blush returned to her cheeks as she looked to the pavement shyly. "It's a hazardous place, my mind. Lots of lists and studying techniques and thoughts of coffee. I doubt I'll have anything nearly as inspired as your thoughts written in there. You sound like an actual writer. I'm more interested in journalism, so I'm better with just stating facts, not really describing things eloquently or-"

He reached out and couldn't help but tilt her head up by the chin. It was gentle, he was barely touching her, but the contact was electric. Swallowing his stomach back down, he forced himself to say, "I know I'll love it."

If she wasn't crimson before she certainly was now. He stared at her for a second longer. It was supposed to be a gesture to get her to face him, but it ended up feeling like more than that. Quickly dropping his hand, he moved himself back a step. Surely he was embarrassing her. She had a boyfriend. He was being too forward.

"It'll give me something to read on my trip," he added, desperate to sweep away that brief awkwardness. "So, thanks."

The usual ivory of her face started to return, as well as a grateful smile. "Trip!" she exclaimed, bouncing as they started heading for his car once more. "That explains the dopey grin! Where are you going?"

"Philly."

"Wasn't Mr. Medina talking to you about some shop there yesterday?"

He shot her a flirty smile. "You certainly seem tuned in to what's going on with me."

She huffed. "I was being confronted by some girl named Paris about my GPA and my life plans before I could leave the room. Man, I thought I could talk fast. That girl could sell Micro Machines."

Paris Gellar was definitely someone he should have mentioned to Rory. Paris had approached him with a similar speech his first day, demanding to know what his plans were for extracurriculars, for college, for his career spanning the first five years. In the few years he had known her, she demanded to know his test scores for every class they shared, frequently assaulting him in the hallway for her answers. He got a kick out of ignoring her, seeing her get even more worked up. He should've known after his discussions with Rory about books that Paris would soon catch on to the new girl's smarts as well.

"Ah, that Paris," he sighed, shaking his head. "She's fun to annoy."

Rory rolled her eyes but smiled. "Well, I don't see becoming best friends with her any time soon, but she seems like she could hold a conversation with the two of us alright."

They made it to his car and he felt a bit of disappointment to have the conversation end. There was no use in denying her enjoyed her company anymore. He all but sealed his growing crush on her with that small touch of her face. _I certainly can't go around hugging her or anything if I'm going to become an idiot just over slightly holding her jaw,_ he thought in embarrassment.

"I hope your trip is fun," she smiled, giving a small wave as she started to walk away. "I want to hear all about that bookshop!"

"You will," he promised.

Watching her face light up at his words, he allowed himself a brief moment to enjoy how soft her skin had felt against his fingers.

* * *

It took a bit of exploring for most of that Saturday morning before he finally found it and from the moment he walked in, he was not disappointed.

Books were stacked, spines facing inward, creating a repeating archway stretching on down several feet. Thin rope lighting repeated every foot or so, giving a faint glow in the makeshift tunnel. He made his way down until he emerged into a large atrium. There were indoor trees with benches wrapped around the bases dotted in the center of the expansive space making it feel like a city park was nestled right in the center of the shop. There were shelves and shelves of books surrounding the 'park', going up three stories, with balconies to look down at the trees below from each level.

Walking deeper into the shop – _warehouse_ was a more fitting term – he noticed small rooms along one of the walls. Inside a few, he saw customers seated on benches, headphones on. Some were reading while listening to their music, but most were just enjoying an album. And that was when he came upon the CD and vinyl section of the building, which was equally as impressive as the books.

He could feel traces of a certain 'dopey grin' on his face and pictured Rory bouncing beside him, teasing him. Most likely, she would be mirroring his expression and just as eager to start weaving around in search of new discoveries. Jess had planned on going a few other places while in town, but now inside the promised treasure of a store he didn't expect to be walking out until closing time.

Mr. Medina had not let him down.

* * *

He got back home around eleven that night, carrying a large sack of goods.

Glancing at the answering machine as he started to head to his room, Jess saw no new messages but he subconsciously stopped regardless. His eyes caught on the small cordless phone beside it and he wet his lips as he considered something. _Would she even be up this late?_

The phone was in his hand, number dialed, and he was in his room pacing before he could stop himself. He balled up his other hand into a fist and chewed on his knuckles as the ringing chilled his entire body.

"Hello?"

Her voice was just as sweet and melodious as always. Something about that made him warm inside a little. "It was phenomenal," he blurted immediately, forgoing formalities.

She didn't waste any time to recognize his voice either. "Details, details!" Rory pressed. He could picture her bouncing around her room very easily.

"I don't think I could do it justice," he confessed.

She laughed. "No way - I can't believe that. Come on, you promised!"

He shook his head. "Honestly. It's one of the biggest bookstores I've ever seen. They got music stuff too."

"I'm a big fan of music stuff. Almost as much as book stuff. But that's it? I know you are usually a monosyllabic prodigy, but I've heard you over books before and now suddenly you can't speak!"

"I'm speechless," he smirked.

She huffed. "Well, then I guess next time you'll have to take me with you."

That response was not what he expected. He certainly wasn't bothered by it. The idea of spending time with her outside of school had definitely crossed his mind. That was before the boyfriend had made his debut and he dismissed the idea for real after their awkward moment when he touched her face. It was hard enough not turning red when she looked at him. How would he react to her accidentally brushing against him while reaching for something in a shop or something?

Still, keeping an indifferent appearance was something he did daily and he was up for a challenge of working harder to keep his composure if it meant spending time with her and hearing more of her thoughts.

"You've talked me into it," Jess agreed.

"Good." He could tell she was pleased. "Now. Onto the business of how you have my number."

He rolled his eyes. "School directory."

"I'm in there already? I just started this week!"

"I suppose I may have had to go online for the most recently updated PDF of it."

"You only suppose, huh?"

"I wouldn't go placing any sure-thing bets on this."

"I see. Well, however the universe decided to gift you with a way to reach me, I'm glad you did. I won't lie, the fact you were bearing that dopey grin over this trip made me excited to hear about it and I don't think I could've waited until Monday at lunch."

"It wasn't a dopey grin. I don't _do_ dopey grins."

"You certainly did _do_ them yesterday."

He liked this banter. It felt easy and natural, as if they had known each other much longer than a handful of days. As much as he wanted it to continue on the rest of the night, he was sure he was keeping her from something. She most likely had to call Dean before bed. It was best to wrap up the conversation.

"Well, I -"

"So did you start my book choice for you yet?" she interrupted.

That startled him. She was offering to continue their chat. On a Saturday night when it was already fairly late. _She really has nothing better to do than talk to me?_ Confused, he couldn't help but grin a little as he accepted the bait.

"I did."

"And?"

"I loved your notes."

She was silent for a long moment and he wondered if she had hung up, until she very quietly piped up with a pleased, "You did?"

The fact she was suddenly as timid as he had been over sharing notes amused him. "I did," he said firmly. "The plot itself felt a bit dry and I couldn't get into it until your notes started popping up."

"What parts were dry?" she asked, seeming intrigued.

In a matter of minutes, Jess had begun his second book dissection session with Rory.


	6. Chapter 6

Their after school walks to Jess's car continued completely by accident.

They would have a book to trade off or a continuation of a story from lunch (those talks had continued by accident as well), and eventually it just became a habit to wait for the other before walking – more _leisurely_ now that it was preplanned – to the parking lot. It was something Jess looked forward to each day now, his small little windows of Rory time before either she hopped on the bus or was picked up by Dean. Sometimes if she was running a bit late to meet him in the courtyard his heart would start to sink a bit only to rise up once she appeared with a red face gasping for air while spurting out apologizes for getting caught up in discussions with a teacher.

Today was one of those red faced days, only it was somehow different. Jess frowned from his position of leaning casually against a tree when he saw a familiar head of auburn hair. He could tell from where he was already her face with pretty red. As she grew nearer, the tears streaking down her face glistened as the sun hit them. He inhaled sharply. This was his first time seeing her cry.

Immediately he started moving toward her, getting to her side in an instant. She looked up at him with red rimmed eyes. She looked embarrassed to be caught in this condition and turned her attention downward quickly, jutting out her jaw a bit as she tried to regain her composure.

"Rory, hey," he said softly, cautiously placing both hands on her small shoulders. "What's this all about? What's wrong?"

He leaned over to catch her gaze and she seemed firmly against it. He repeated her name and she finally turned toward him. She chewed the inside of her cheek for a moment before exhaling.

"I got a D," she frowned.

"A D. On what?" He started to think what classes she had that day.

"Chemistry. Jess, I don't get D's."

He wanted to smile at how adamantly she had declared that. It was cute. He caught himself before he did, afraid she would read it as him being dismissive. Instead, he tentatively reached out with one hand to wipe some of the tear stains of her cheek. After one smudge, he shot her a questioning expression, wondering if it was okay to be touching her like this. She didn't make any moves to stop him, just stared back. Something about her gaze seemed a bit scared, but he found her almost unreadable in that moment. She had never been upset like this. After another smudge, he took a step back from her.

"Look, it's a tougher school," he began, "It's bound to be a step up from what you're used to from your last school."

"Did this happen to you?" she demanded to know.

He hesitated. "Not quite a D, but I did take a bit to adjust to being able to… express my opinions more."

She frowned deeper. "What do you mean?"

Jess sighed. He didn't really want to admit this part of himself to her. Talking books and music and movies had become second nature, but talking about his life didn't seem quite as easy. "I used to skip a lot," he muttered. "A _lot._ I hated my school. I'd try to give deeper meanings to the curriculum and expand outside the scope of projects but they didn't want that. They wanted basic. I didn't want to _be_ basic so I stopped turning things in and usually ended up skipping."

Rory seemed surprised at this. "You figured doing nothing was better than doing the actual assignment? I mean, you could've just coasted along."

He shrugged. "I just didn't see the point if I couldn't be challenged to do more. I was young and stupid. It took Nathan kicking my ass and getting me set up here to get that challenge I wanted. And at first, I did the work I had first tried doing at my old school – what I thought was deeper and 'meant stuff'. And they didn't think it was terrible, but I wasn't receiving exactly the marks I thought I was going to. I talked to some of the teachers, figured out more of what I was allowed to explore and do and I just… started to challenge myself.

"It took some adjusting. My slacking off for a bit at the last school made me a bit rusty at first, but now I'm glad I tried and stuck it out."

Rory's eyes widened as she listened. Her tears had stopped and she seemed to be calming down. She even gave a teasing grin. "I should cry more often. I think that's the most you've ever said about yourself."

Jess smirked. "Don't get used to it."

She giggled, then looked back to the ground with a sigh. "Well, I guess I have to try harder."

"Rory, is everything alright?"

The voice was unexpected and startled them both. Rory looked over and tried to smile as Dean was quickly approaching them. Jess hadn't officially interacted with Dean at this point. It had been several weeks and he supposed it was finally time. _Let's see who this guy is who managed to land Rory Gilmore,_ he thought with a hint of envy.

Dean gave Rory a tight hug and a soft kiss on the lips. Jess did his best to avert his eyes, not really in the mood to see that kind of interaction.

"I got a D," Rory said unhappily, catching Dean up.

The giant of a boy looked incredulous. "A D? You don't get D's."

Rory turned to Jess, tossing him a smirk. "Told you."

Jess matched the smirk.

Dean shook his head, brown hair tossing about as he did. His eyes were full of disbelief. "No, seriously. You're the smartest person I know, Rory. It's a mistake. It has to be. That's somebody else's D – the teacher mixed up the papers or something, right?"

"It's a lot harder material than Stars Hollow High had," she tried to explain, picking at a strand of her hair. "I just need to study more."

Her boyfriend grunted. " _More_? You always study like crazy. It's all you _do!_ "

"That's not true," she said quickly, hurt in her eyes.

"Seriously, you study _all_ the time. It doesn't make sense for you to get a D."

Jess's eyes narrowed. He was starting to feel a bit bothered by the interaction. It felt like he was a third wheel and he would have just said a quick 'later' and walked away, but Rory was getting upset again. Her face had already fallen considerably again the more Dean said to her. Jess wanted to make sure she felt at least somewhat reassured before he left them. He had an idea.

"I can… help you study," Jess interjected slowly, then gave a small shrug. "Or whatever."

Dean and Rory both turned to him, surprised. The tall boyfriend seemed to just now catch thst someone else had been standing there. A glimpse of annoyance flickered in his eyes as he took in the length of Jess. "Oh, hey," Dean frowned, sticking out a hand. "I'm Rory's boyfriend, Dean. And… you are?"

"Jess." He shook Dean's hand and turned to Rory, his expression softened. "I'm serious. I can help you get more comfortable with the material until you get your grade up and get used to how to do the assignments. You can come over Friday if you want. Go talk to your teacher first and see what he thinks and then we can work on it all night."

That seemed to bring her back to the calmed down point she had been in before Dean arrived. She nodded happily and took a sigh of relief. "Thanks, Jess. I'll do that. I'll talk to Mr. Haufman tomorrow and then we'll study Friday."

He nodded. "Happy to help."

Their usual walking time had been interrupted now that Dean arrived, so Jess quickly excused himself and began the trek alone to his car. It felt weird to walk it alone after becoming so accustomed to Rory's bouncing and cheerful demeanor beside him. He already found himself missing their banter.

"Jess!"

He spun around to see she had run after him. They were now a quiet away from Dean, and the look on the boyfriend's face showed he was just as confused about it as Jess was. Jess focused back on Rory and raised an eyebrow.

"Chasing after me in front of the man candy. Tsk tsk, Rory."

She scrunched up her face at him. "Joke's on you," she retorted, finally starting to seem more like her usual self. "I ran over here to point out to you that you basically invited me over."

Her eyes gleamed and a small, playful sneer covered her face. He went to open his mouth to shoot something back at her quickly, before recognizing that she was right. He felt his face flush and he blinked quickly, backtracking in his head. _...work on it all night…_

"I never..." he started, finding himself dizzy at the thought of her in his house. Her? Beautiful, charismatic, intelligent her standing inside his dumpy, crack den of a house? He finally found his voice again, but possibly an octave or two higher than he meant. "I don't remember specifically mentioning my place."

She laughed, and he knew she was aware he was flustered. "But where else would we work _all_ night?" she pointed out, giving him a gentle jab in the chest with a finger. "Library will close, public places will be too noisy. So, again I say, you invited me over."

He worked his mouth around a bit, annoyed with her but also admiring of her catching him in this. _Well, I'll have tonight and tomorrow to clean a bit before Friday_ he assured himself, but it didn't make the brick in his stomach go away.

He caved. "Alright. So I did."

Rory beamed, and that alone made caving worth it. "Okay," she practically sang, satisfied. Walking backwards returning to her boyfriend, she gave a wink and added, "I can't wait to see this library you've inherited."

He stood there watching her link arms with Dean and walk away together, a picture perfect idea of a couple. Though he felt a pang of jealousy, Jess reminded himself he had no reason to think she wasn't being treated well and if Dean made her happy, that was all that really mattered. Though, he did feel a slight victory at the thought that Rory would be his private company Friday and for some reason, that felt like enough to hold on to for now.

* * *

Jess didn't think he had ever inhaled so much bleach.

It took a lot of time – time he could have used working on assignments – but he got the house somewhat presentable as well as his car, seeing as he would be escorting her in it. He couldn't remember the last time he had company over and certainly wasn't going to make a bad impression on the one person starting to matter a lot to him.

He nervously waited for her in the courtyard Friday. He raked his hands in his dark hair over and over, only fluffing it out even more. _I feel ridiculous. You'd think she was the Queen coming over for tea or something._ But he knew it wasn't ridiculous. Rory meant a lot to him. Her opinions mattered, some of them more than he wanted them to.

She appeared next to him and they began walking. He noticed an extra bag with her and wrote it off and most likely being clothes to change into, as well as – knowing _her_ – extra note cards and highlighters. Rory certainly was nothing if not thorough.

They climbed into his car and he began the thirty minute drive, The Clash playing at low volume as they chatted away. Rory had gotten the details of what her chemistry teacher was looking for and it matched up to what Jess had remembered when he took the class the previous semester. They got off topic for a bit, slipping into their easy and playful back-and-forth, and Rory even managed to get a complete laugh out of him – something she made a point to mention and proclaimed it was her finest victory as of late. He agreed.

He pulled into the driveway and shut off the car. His breathing hitched, knowing this was finally it. Knuckles whitened on the steering wheel until Jess finally let out the air from his lungs and opened the door. Rory quietly followed suit, seeming to understand this was big for him. He hoped she didn't read into it too much and only assumed he was nervous over the house itself. Not her being inside of it. With him. Alone.

Jess let the door swing open, waving an arm to signal for her to step inside first. She did, her careful blue eyes surveying the living area. He quietly observed as she took in the worn couch he had thrown a clean blanket over, the outdated television he barely used, the coffee table with obvious cigarette burns he couldn't scrub out and faint markings of beer cans decorating the top. He sighed, knowing he had done the best that he could.

Wordlessly, Rory went into the dining room, setting her backpack on the dining table and looking back at him. "Mind if I change my clothes first?" she asked.

If she was bothered by her surroundings, it didn't show. Her usual easygoing demeanor remained and she seemed genuinely happy to be here with him. His nerves seemed to calm a bit.

He gave a short nod and motioned for her to follow him. "You can change in my room," he said. "Let me grab a shirt and some jeans and I'll change in the bathroom."

Her eyes lit up as she followed him into the bedroom, carrying her clothing bag. "I've never been in a boy's room before," she snickered, waltzing in as if it were her own. As expected, she raced over to the bookshelves.

Jess seemed taken aback. "Never been in your boyfriend's room?"

Rory blushed quickly and gaped for a moment. "I – we – no, we don't -" She started to open and close her mouth repeatedly, not knowing where to begin to respond to that. Jess chuckled, fully enjoying this rare speechless Rory moment. Usually she'd quickly change the subject or have a witty remark.

"Who knew the idea of sex could fluster Rory Gilmore so easily," he commented, shaking his head as he pulled out some of his clothing. "I suppose that's why Tristan insists on calling you Mary? On account of being so virginal and all?"

She finally seemed to find her tongue. "I've… done things," she insisted.

"Careful with those descriptions, you're getting my heart racing."

She huffed, picking a book off one of the shelves. "Is this the library you got?" she asked, clearly ready to move on now that she found herself able to speak again. She put the book back and glanced over the stock. "From the way you spoke, I guess I assumed…"

"There'd be more?"

"Well, yeah."

"There is." He gave her a grin and started to leave the room. "There is," he said, "but that's for later. Get changed. We've got chemistry to work on and I believe I insisted it be _all_ night."

He shut the door before she could press for details and holed himself in the bathroom to change.

A few minutes later, he busied himself pulling out drinks and snacks for them. He even managed to dig up some of his old chemistry notes the other night and had them out to see if they would bare any weight now. He almost dropped what he was carrying into the dining room when he looked up and saw Rory suddenly standing in front of him.

Jess was used to the sight of her taking his breath away by now, but he had only ever seen her in their school uniform. And school girl fantasies aside, it became such a regular thing, he hadn't ever pictured what she _would_ wear outside of school. She had on a casual black knee length dress with a cardigan the same blue as her eyes pulled over it. The gray pantyhose she had worn for school were gone, just simple black flats on her feet. She always looked smart in her uniform, but now she stood in front of him looking mature and confident – and dare he think _sexy_ – a hint of the woman she might grow to become. He felt young and immature standing near her in his old band shirt and jeans.

"Not so virginal now, huh?" She stuck her tongue out.

Finally managing to move again, his shook his head with a smirk. "Definitely not."

His words made both of them flush and they immediately went to work pulling out books and supplies across the table. They sat down side by side, as Rory began giving him the rundown of what she thought might be the best approach to the evening's goal of mastering chemistry. All the while Jess inhaled her perfume and thought to himself this was the closest he had ever been next to her.

It was inevitable they would take a break to have an actual meal, not just snacks. Rory made a point of announcing she would pay for the pizza since he was doing her a favor by giving up his Friday night to tutor her. He let her pay, not mentioning he was more than happy to spend a Friday with her no matter the circumstances. Spending time together at school was one thing, but seeing her in a more comfortable setting felt new. He drank in the experience unsure if he would get many of them.

When the pizza arrived, they plopped in front of the TV and chose a movie to watch merely for critiquing purposes. It wasn't too far along in before Jess was practically ranting.

"It's the same contrived plot every romance tries to do," he moaned, making a show of rolling his eyes.

Rory seemed to disagree with him, which always led to some of their best discussions. "There's always got to be some kind of tragedy in a romance though," she insisted. "Something to bring things to a head. Otherwise it's just a story about two people bickering until they get together."

"It's exasperating," he grimaced, taking a sip of his drink. "There should be more."

Rory tilted her head at him as she swallowed her bite of food. "More what?"

He felt the pressure of her eyes on him and quickly tried to gather his thoughts. "Well, _depth_ to the relationship. That's why these kinds of films bland. You see them flirt a bit, they're obviously attracted to each other, but what do they _talk_ about? What's left to talk about after they've argued and hated each other for months then finally get together? That's the problem with a lot of these romance movies is they don't show enough actual connection with the characters to make you want them together. They never really _talk_."

Rory didn't respond right away which was definitely new. He glanced over and noticed she was staring forward, yet not at the screen anymore. She wasn't even touching her food anymore which was probably the most surprising. Jess frowned and tilted himself toward her a bit.

"I mean, come on. You've got to see the difference between a movie romance and a real-life one, right?" He paused, thinking of the next question he wanted to ask; the one he had wanted an answer to for awhile now. "What do you and Dean talk about?"

She snapped her attention to him quickly, eyes big and almost of the look of offense in them. "We talk about things," she finally said with a stiff tone.

Jess snorted. "Using your same descriptions from earlier I see."

She tossed the remaining half of her pizza down on the plate and narrowed her eyebrows. Adjusting herself to face him better, Rory gave him a hard expression. "We _do_ ," she stated firmly. "Like, he plays sports and I'll listen to him talk about practice. I go to the games sometimes too."

"Do you _like_ sports?"

"Well, no. But I'm supporting him by going to them, aren't I? That's something."

Jess leaned forward. "Well, what _else_?"

He could tell she was really searching for examples when she kept leaving long pauses. Her face contorted as she thought and reasoned within her head, piecing together how to respond. "We talk about school. Well, I mean, I talk about going to Harvard and he tells me how smart I am." Her face changed, starting to grow upset. "Which, I kind of hate… because it feels like he doesn't get it's still a lot of pressure. Just because I'm smart doesn't mean I can't mess up and do something wrong like… like maybe I _won't_ get into Harvard… or I mean, look, I got that D..."

The anxiety was growing in her voice and he felt a pang in his chest, realizing he had kind of instigated it. Nervously, he reached out to pull her into his arms and held her deeply. They had never embraced before – he wasn't sure if they were those kinds of friends or if it was wrong to do because of her boyfriend. But she was starting to cry again and he knew she needed it. Her face burrowed into his chest as he continued to comfort her.

"This D has really messed you up, huh?" he murmured.

She choked out her words, body starting to shake a little with each sob. "My mom and I have just had a plan for me for Harvard my entire life, and what I'm going to do, and I've just always been told how smart I am and I read lots of books so I _must_ be a smart girl and then I got a scholarship to Chilton so I _definitely_ must be a smart girl, and all these people constantly telling me how smart I am and then I get my first bad grade and nobody says it's okay, that everybody gets bad grades sometimes – no, they just expect me to keep being smart and obviously it's someone else's fault because I am supposed to be perfect and have this perfect life plan and - "

He had to stop her. Seeing her like this was too much. "Rory."

She stopped her sobbing rant to pull her face away from his shirt and stare at him. He had never seen her look lost and unsure before. This was a girl who always had a plan and an answer for a problem. She seemed more human somehow.

"It's okay," he whispered with a sad smile. "Everybody gets bad grades sometimes."

She gave a small chuckle and looked away, embarrassed to finally be told the very thing she had wanted to hear.

"No one's asking you to be perfect. You're just tough. We all know you'll bounce back and learn from anything bad that happens your way." He paused a moment. "And if anyone makes you think you need to be some perfect Barbie girl or whatever, well, I'll kick their ass."

She gave a more spirited laugh that time. "Hey, I said I wasn't always going to be a damsel, remember?" she pouted jokingly.

He smirked. "I seem to remember I'm supposed to be more of a sidekick."

Rory giggled again and wrapped her arms around him back, placing her head delicately on his shoulder. She let out the breath she had been holding in. "That's right. Sidekicks give motivational speeches when the hero is feeling lost."

"Exactly. I know my place."

She held him a bit longer than he expected her to. It seemed like it was going to be a hug, but she wasn't pulling out of it in a rush. If anything, her grip kept getting tighter. His heart hammered wildly. Several hours ago, he thought just sitting in a chair next to her was their closest contact, and now this. Things were going to be different. It was going to be harder to tell himself she was out of bounds now that he had held her this close. Her entire body was warming him completely and he was beginning to dread the chill that would take over when she finally had to pull away.

He seemed to jinx himself as in the next moment her cell phone rang. She jolted away from him, staring at his face with shock as she retreated to the far side of the couch. He gave her a steady gaze, void of emotion. The ringing hadn't scared him as he had somewhat expected something to ruin the moment sooner or later. The look on her face made it seem she was just caught doing something she wasn't supposed to. After another second, she scrambled to get up so she could grab her phone off the table.

Shaking his head, he rubbed his palm against his forehead. It had been one thing to sometimes dream of holding her like that, to think of the various ways it might happen, but another to feel her against him like that.

This was trouble.

"It's only a quarter to nine," she was saying into her phone. Her voice sounded pleading, with a hint of annoyance. "I was hoping to stay at least another hour or so. We were just in the middle of a break and I still wanted to cover -"

Whoever it was on the other line was cutting her off. Jess watched as anger cross her face, before a look of exhaustion and compromise.

"Fine. See you in a bit."

She snapped the phone shut and made a loud groan, throwing it on top of her bag. Her hands came up to rub at the sides of her head. "Dean wants to pick me up now. He's on his way."

Dean? Jess had been almost positive it was her mom thinking she was out too late.

"You don't seem happy about it," he observed.

Rory came back over to the couch. She collapsed with another groan, clearly defeated. "I'm not. I mean, I am, but I'm also not. We're just -" She looked at Jess sadly. "We were having a good time. I thought I could stay a bit longer. I mean, this is our first non-school hang out, you and I."

He gave a look of surprise, like he hadn't been aware. "Do you think we'll be allowed _more_?"

She laughed and gave him a stern expression. "Be nice. I mean, I'm glad he wants to see me for a little bit tonight, but he knew we were doing this study thing. I guess I just thought he was going to pick me up later and then I'd hang out with him tomorrow."

Jess didn't say anything, just continued to watch her. She seemed to catch it, becoming a bit unnerved by it. "He really is nice," she said quickly. "He calls me every day and walks me to the bus stop in the mornings and gets me coffee. We sometimes go out places when I've finished all my school stuff. I have a lot more school stuff now so less time and he hasn't been too keen on that."

" _Not-Too-Keen Dean_ , they call him," Jess quipped.

She shook her head at him before perking up sharply. "Wait, the library!" she practically yelled. "Dean will be here soon and I still haven't gotten to see it!"

Jess gulped. He certainly hadn't wanted to rush the experience of showing her the collection he had been given. It was the one area of the house he took extra care setting up. The space had been set up nice before, but he knew Rory would appreciate it as much as he did, so it made making the extra efforts worth it.

Unsure how much time they had, he knew he needed to make the most of it. "Okay."

His hand took hers and they moved to a door off of the kitchen. He opened it to reveal stairs and they carefully descended into the darkness. Leading her steadily, he made sure she took each step before he moved forward while trying not to dwell too much on the fact he was holding her hand in his.

"We can't turn the lights on?" she wavered, unsure of the darkness.

"It's just a couple steps more. It'll be worth it, I promise."

They got to the bottom of the steps, still swallowed in the lack of light. Her fingers pressed all around his own, begging him not to let go and leave her in the darkness alone. Remembering where the switch was, he quickly leaned over and flipped it before turning back to wait for her reaction.

The basement illuminated, but he was certain it wasn't in the way Rory had anticipated. He watched her as she took in the delicate lighting glowing amongst shelves and shelves of books. It was set up almost like a typical high school library, with shelves alone the walls as well as forming isles. A lounge area in the middle of the space had an old fashioned lounge chair, a table with a lamp beside it.

The lighting was bright enough for reading, but low enough for atmosphere and a possible nap between chapters. This room alone was the only reason he refused to smoke indoors. No habit was worth potentially wasting all of his books. The books that Nathan had given him.

Jess waited to see what Rory would say, but was happy to find he had rendered her speechless for the second time that day. Awestruck, she let go of his hand in favor of wandering around the library. As much as he hated to lose her grasp, the exhilaration on her face made him reflect it on his own. She moved past aisle after aisle, looking up and down in awe at how many books each set housed. She went to the lounge seat and rubbed the fabric with an open palm.

"This..." Her voice was barely a breath as she trailed off. Moving her eyes away from it all and back on him was no easy feat. Her eyes were full of questions, her mouth struggling to form one of them into words. "How..."

"Do I have such a kickass study hidden inside a crack den of a house?" he offered, slowly approaching her. He shoved his hands deep in his pockets and gave a small shrug, lazily casting his eyes to hers. "Parents aren't around. Nathan left some cash so I could properly contain his collection. Man would be rolling in his grave had I not gone a bit… splurgy."

Rory's eyes were sparkling, a mix of the joy and the mood lighting reflecting on them. "This is incredible, Jess," she praised breathlessly. She shook her head. "Seriously, how many books are there? Have you read even _half_ of them?"

He smirked. "I'm sure I knew a number once bit I don't remember it. I knew Nathan for a long time and I definitely have read a good chunk of these, but I'm sure it will take the next bit of my life to tend to them all."

"Hmm," she mused, pretending to think hard on something hyperbolically. "Well, should you ever need help reading them all to find the extra special ones I just may know a person."

Jess's steps grew nearer to where she was. He played along as he always did. "I'm sure I could allow something like that," he nodded with a cool tone to his voice. "Should the proper person come along and all. May be hard to track down the right one."

She nodded in agreement, feigning a serious demeanor.. "This person would be great for the job. Has already reviewed a few from this collection and only had good things to say."

When he stopped, it was dangerously close to her and he knew it. The barrier he had usually kept in place felt disarmed for now. Holding each other earlier had disabled it, or at least given him the bravery to test if it still was. It was hard to tell in the light if she was flushing or embarrassed, but she definitely wasn't running.

"I never did get a good answer," he said softly. Her lashes fluttered as her eyes searched all across his face, not getting what he was referring to. He was pleading with himself to lean forward, to test these new boundaries further. _How close will she let me get?_

But first, he had to know.

He asked carefully, "What _do_ you and Dean talk about?"

Rory's mouth parted cautiously, and she ran her tongue over her lips to wet them. He was mesmerized by the unexpected gesture and felt himself go numb. It almost even felt like she was starting to edge closer to him.

Her voice was barely a whisper. "We -"

A deliberate knocking sounded upstairs. Jess cursed under his breath and started heading upstairs. He couldn't turn to face her right then. She had looked so kissable, so beautiful in those last few minutes and he wasn't going to be able to pull himself away if he saw her in that room again.

Dean and Jess stood awkwardly by the front door while Rory gathered her things in the dining room. The boyfriend didn't seem entirely comfortable being there, but he also wasn't being rude. He rocked back and forth on his heels, surveying the living room and keeping his eyes off Jess.

"So, uh, thanks for helping her out, man," he eventually seemed to force himself to say to break the silence. "She really appreciates it."

Jess gave a short nod. "No problem. She's a good person. Happy to help."

"It's just crazy. She doesn't _get_ bad grades. These things don't happen to her."

"Everybody gets bad grades sometimes."

"Not Rory."

Jess felt his brow furrow. "Sometimes pressure can be a bit much."

"She can handle it."

He started to see a glimpse of the attitude the people in this girl's life had. Because Rory had always preformed well, they kept expecting her to do so, like a well oiled machine. There didn't seem to be any room for a small malfunction now and then.

Rory emerged with all her things and a smile plastered to her face. After an entire evening seeing her _laughing, excited, victorious, in awe_ … this smile didn't appear real. It felt different. This wasn't a smile Jess got from her. This was more of a routine smile. _Expected_.

"Okay, I'm ready," she announced, as if they couldn't tell.

Dean made a half-hearted attempt at a goodbye to Jess and was out the door in a heartbeat. Rory lingered behind a moment, shyly looking at her tutor. Jess felt himself at ease again to see a more genuine expression from her.

"Thank you for helping me tonight," she said. "And for showing me your library."

"Anytime. You'll let me know about that _someone_ who can help me read them all?"

She scrunched up her nose. "I'll let you know." Out of nowhere, her expression got even shier. "Jess." Her voice was very still. She seemed uncomfortable. Her words were quiet and soft when she finally continued. "Are you… alone a lot?"

The ' _my parents aren't around_ ' line had briefly been ignored and he had fully expected it to be brought up again. She was too caring to let a line like that be a throwaway. It wasn't something he wanted to delve into anytime soon. He trusted her and liked her alright, but sharing was a lot for him.

She seemed to understand what he was thinking, because she didn't wait for an answer. "Well, you have me now, so you don't have to be alone sometimes… if you don't want to be."


	7. Chapter 7

" _Well, you have me now, so you don't have to be alone sometimes… if you don't want to be."_

Similar words had been said to him before.

He had been seven when his parents had started fighting, and it wasn't long before Liz and Jimmy took turns not being around while they figured out whether to split up or work it out. Sometimes one of them would be too angry while drinking, so Jess would grab a small bag, fill it with books and a blanket, and go down to an old bridge close by. He would curl up right at the edge of it, dangling his feet above the water with the blanket around his shoulders while he read in peace. Eventually, Jimmy stopped coming back home. The gaps when Liz wasn't around grew larger. Sometimes it was because she was working. Sometimes she was off with a new boyfriend.

For awhile, Jess would camp out on the porch while waiting to see which parent was coming home so he could get an immediate inspection of their mood, giving him time to sneak off to the bridge if necessary. He would sit right on the first step, his attention deep in a book every day until it became too dark to read. Sometimes he would just sit and wait longer, without reading, but eventually it felt too lonely so he would go inside.

It was during these porch readings that Jess started to notice an old man who would walk down the street in the late afternoon with his dog. Jess ignored the old man, remembering school telling him not to talk to strangers, but after awhile he grew curious. He started staring at the man as he passed. The man began to stare back every time with an equally troubling frown. One day, the old man came right up to the start of the driveway, and placed a book down before walking away. Jess waited until the old man was long out of sight before scrambling off the steps to get it.

He had finished the book within a day and placed it back exactly where he first received it a few minutes before he knew the old man was due to pass by. He crawled back up on the porch and clasped his knees, waiting with his intense stare.

Sure enough, the old man came by with his dog, picked up the book and deposited another much to Jess's delight. He didn't own many books and the library at school only had so many within his reading level which was vastly superior to his classmates. These new books were challenging and had new ideas and words he had been waiting for.

This tradition went on for a few weeks, becoming the one constant Jess could come to rely on. At one point he finally called out to the man, introducing himself first. That was when he officially met Nathan.

One night, a book was waiting with a small wrapped plate beside it. Again waiting until Nathan was completely out of sight, he uncovered it to find a piece of still very warm lasagne. It was the first warm food he had seen in awhile and immediately his stomach growled. He was halfway through it before Nathan and his dog came up along the other side of the street, making their way back to their home.

Something must have finally lined up in his head, because the old man stopped, crossed over, and stood at the end of the driveway. He face suddenly looked very sad amongst all the wrinkles, his eyes deep and serious.

"Tell me, Jess," he started in his rasp of a voice. It was obvious this man had been smoking for a long time. "Are you alone much?"

Young Jess had shrugged before taking another bite of food. "What is much?"

Nathan gave a chuckle and grew quiet for a moment. "Look, kid, I have a lot of books. If you ever want to come pick one out yourself instead of me picking them for you, you can. I'm sure you're growing used to being on your own now, but doesn't mean you don't feel lonely sometimes. So… my house is right over there. That yellow one. I'm pretty much always home, too, so if you ever need anything… I'm around."

Jess had gone the next day to pick a book.

* * *

 **A/N: Thank you so much for the reviews and just reading my story in general! It's made me happy to work on it and get it out to you that much sooner. This is a shorter bit just to give my thanks and a few shout outs.**

 **Emily: I agree about slow burns. I like seeing more reasons WHY I should be shipping a couple. And I personally believe a person becomes more attractive to you as you bond with them and get to know them. Also - introverted comrades, I loved it xD**

 **Droolia: You know, I did kind of forget Rory's eating habits for a sec haha. I kind of got bored with a lot of stories on here constantly mentioning it that I didn't want to fall into that too. But let's just pretend she found him interesting enough that it was worth not pigging out for a meal :P**

 **Nancy: Thank yo for saying I'm capturing them pretty well! I try to picture them saying things in my head and if it fits.**

 **I am seriously smiling a 'dopey grin' every time I see these reviews, so please keep them going if you have a moment.**


	8. Chapter 8

Rory's chemistry grade began to improve and by mid-terms, she was plenty confident in handling assignments on her own. The study sessions ended, much to Jess's chagrin. They had English class, lunch period, and briefly after school to chat still, but he kept thinking of things he wanted to do with her, things to share with her that _weren't_ at school. He thought his growing crush on her would become too transparent if he bothered to ask. The constant embarrassment and blushing she caused in him felt so difficult to hide at times.

The spring semester was quickly coming to a close. With only two weeks left, major projects were keeping everyone occupied. Jess didn't mind most of the assignments, but the English one, for once, was sadly the one he wasn't enjoying. They were paired off in groups of five and each group was assigned a section of Romeo and Juliet to perform, preferably their own interpretation or adaptation of the scene. Rory's group, however, seemed to be going the more traditional route.

"I don't know why Paris won't let us try at least _something_ a bit different," Rory sighed with frustration. She chewed on her sandwich across the table from Jess, giving him the rundown of her group's project. "She thinks Elizabethan is the only way it should be interpreted. At least _your_ group is doing something interesting."

He rolled his eyes as he looked away from his book. A pen was poised in one hand, the other holding the book open from the bottom. He was adding a few more notes in this one before lending it off to Rory. He gave a scoff at the mention of the project he wasn't thrilled about. "Shakespeare's dull anyway," he commented as he scribbled another quick thought down. "Doesn't matter what you do to try to improve it. Still sucks."

Rory gave him a baffled look. "How much of him have you actually read?"

"Enough to know he's dull."

As he expected, that didn't satisfy her. "What about -"

They were interrupted as Paris appeared in a whirlwind beside Jess, slamming her palms down to brace herself. Her small frame knocked into him briefly as her position stabilized. Edging away to regain his space, he shot her an irritated glare that she clearly missed. Her brown eyes were focused instead on Rory.

Paris's presence wasn't new. Her and Rory somewhat got along now, after a semester of on-and-off bonding. They had a lot of classes and after school activities in common, so often Paris would appear while Jess and Rory were having lunch or talking before English class. She didn't interrupt all the time, but sometimes it was right in the middle of an interesting conversation and Jess refused to hide his annoyance on those occasions. Paris was usually a very on-edge and demanding person, but something felt even more off today.

She seemed to finally quell her rage long enough to speak. "Tristan got expelled."

The Prince was gone? That didn't seem right. The DuGrey's were old money and were well known. What could Tristan have possibly done to get in so much trouble not even money could get him out of it? Jess was curious enough to want to ask, but didn't dare to. When Paris was focusing in like this, it was better not to interrupt.

Rory frowned. "What about our project? The performance is this Friday night."

"He was our _Romeo_ ," Paris yelled at no one in particular, slamming fists down. Her mouth twisted into it's usual glower. "The _only_ boy in our group and he gets his pretty little ass kicked out! Totally unreliable." Her scowl was unmistakable as she stared off in deliberation. "They couldn't wait _one_ more week to ship him off to military school? This is jeopardizing my chances at Harvard and if I don't get in, you damn well better believe I will come after him! Now I'm going to have to spend the rest of lunch trying to figure out how we're going to save our grade."

An idea seemed to strike her out of nowhere. Her hair bounced and sprang to life as she swung her full attention to Jess. She gave a large, menacing smile. He stared back at her, growing uncomfortable. Paris didn't usually smile. And she sure enough never smiled at him.

"You." She jabbed a finger at his chest. He swatted it away and she brought it up again, jabbing him again. He shifted back from her, losing his patience. Her eyes were steady. "We're going to get you in our group."

He scowled. "Why? I like mine just fine."

"That's because you only have to say one line," Rory said with a laugh. She was finishing her lunch quietly for the most part, enjoying watching Jess being tortured. Her eyes were playful while watching the development before her.

"Exactly. It's the role I was born to play," he agreed. He wouldn't mind being in a group with Rory, but he knew Paris was directing their group and he was not interested in her snapping at him if he didn't capture Romeo's spirit well enough, costing her a good grade. He knew Paris enough by now to know anything he delivered wouldn't be enough.

Paris kept on, jabbing him once more. "Your group has mostly boys. _We_ don't have _any_ boys."

He rolled his eyes. "This sounds like the set up to a math problem."

Paris was already gone. He stood up, searching to see where she ran off to so quickly, but she vanished into thin air. Feeling uneasy, he sat back down and shot Rory a concerned look. "What exactly do you think _that_ was all about?"

He found out _exactly_ what it was about the next day when Mr. Medina told Jess he was switching Jess into their group to make up for Tristan being gone. Luckily, Jess's group had one extra person anyway, but he strongly suspected Paris had worn Mr. Medina down until he caved. He had no proof, but the teacher's eyes seemed to be looking around uneasily a bit as he mentioned the change in plan before class.

It wasn't the worst chain of events to happen, but Jess felt a mix of emotions once their groups split off to rehearse and he discovered Rory was playing Juliet. On the one hand, the kiss scene Paris was insisting on was hopeful, but he had a strong feeling Rory's boyfriend would be in the audience and that made the only highlight of being in the group no longer worth it. _I can picture his reaction to it now,_ Jess thought with a sigh. _Even if it's a quick kiss he'll read something into it. Rory's_ his _girlfriend after all. Her only identity._

"We're practicing after school," Paris ordered as class drew to a close. "No exceptions. I won't fail this assignment just because we got a new Romeo two days before the performance. The only problem is we can't use the gym or the stage to practice today so we need to figure out another place to go."

Rory chewed on her lip thoughtfully as she set down her play booklet. "There's a dance studio in my town. It's about thirty minutes from here, but it's always free after seven on weeknights."

"Perfect." Paris wasted no time agreeing to it. "Rory, right down your hillbilly dance studio address down for everyone, and Madeleine, Louise -" she glared at the two other girls in the group, "- don't spend all night putting on makeup getting us off schedule. I won't tolerate any tardiness especially if your excuse is wanting to look _cute_."

Madeleine groaned. "There's only going to be one boy there," she pointed out while continuing to file at her long nails. "And he'll be pretty tied up with Juliet."

"He was _before_ becoming Romeo anyway," Louise said under her breath, twisting a strand of hair in boredom.

The girls had both shown interest in Jess when he first arrived at Chilton, but when he made it clear he didn't return the interest they were quick to scowl at him when possible. They didn't seem happy with the fact Rory ended up being the one person his attention was drawn to.

The bell rang and Rory and Jess gathered their things before walking out together, eager for a new atmosphere. Paris zipped past them in a hurry, the whiplash sending them teetering. "What is she on that gives her so much energy?" he mumbled, stabling himself.

Rory giggled, shifting the books in her grasp. "I won't question it.. I'll even gladly step aside and let her do whatever she wants on this project. Anything to make my summer with her easier."

"The Class Representatives thing? That's in Washington, right?" He had almost forgotten.

Student elections had been the week prior and Paris won the senior class presidency, with Rory as her vice president. There was a conference all the new electees had to attend to learn leadership and skills to help them in the coming year. The conference would take up most of the summer, keeping Rory busy enough that contact would be limited. _Not like she'd be able to spend a lot of her summer with me regardless_ , he reminded himself. Plus, he was happy for her to get the opportunity. He just wanted to think of a way to still fit into her summer somehow.

"Yup. We leave almost right after school lets out and we'll be gone six weeks." Rory paused, slowly comprehending the reality of the situation. A mask of horror covered her normally delicate facade. "Six weeks of Paris." Her voice grew hollow as she clutched her books to her chest even tighter. "Six weeks in a room with Paris."

He chuckled. "I'm sure you'll be braiding each other's hair in no time."

She sighed, quickly looked over at him, her eyes intense. "I'm going to need a _lot_ of books to keep me sane, so you better start getting a pile together for me. I'm talking more margin notes than you've written in your entire life."

"Oh really?" He made a show of looking offended. "Gonna demand more than one book just like that? I don't think I signed you up for a library card." When she gave him a tight mouthed, clearly 'over it' response, he lifted his hands in surrender and smirked. "Alright, I'll see what I have that will soothe you in your time of desperation."

She seemed pleased to hear that. They walked a bit more and he realized they would be going to their separate classes once they hit the next hallway. She would turn left and he would keep going straight. A thought came to him and he wanted to mention it before they parted.

He cleared his throat. "We could also… write letters if you want."

"Really?" Rory spun to her whole body toward him, stopping completely. Her steely blue eyes were big and shining. "That'd be really cool! I mean, who gets the chance to write letters anymore? We'll be temporary penpals!"

He nodded. "There's something more romantic about a letter anyway."

It was out before he meant it to be and he was quick to back pedal. His face felt hot as the words fought to make up for his brief transparency. "I mean, all the greats wrote letters and a lot of them were published," he went on, nervously running a hand through his hair. "It's just a more personal and stylistic way to communicate."

"Agreed," she said, seeming not to have caught his initial embarrassment. Checking the clock on the wall, she flashed a disappointed look at him. "Gotta get to the next class. Hey, if you want to you could just come hang out for a bit before we rehearse tonight. There's a diner we could eat and study at, oh and maybe I could take you to that bookstore I've told you about!"

It was the first time she had extended an invitation for him to visit her small, off-beat town that she was always mentioning to him. Trying to morph his instant wide smile back down to a grin, he asked, "Dean's not picking you up?"

"Nah, he was work after school. I was planning on taking the bus."

"Oh, I get it." Jess nodded a teasing smile forming slowly. "Lover boy can't chauffeur you today so you're getting me to."

She laughed and swatted at him. "Oh, shut up! Can't I just want to be around you a bit more?"

The hallway was nearly empty, the bell threatening to chime as they both watched each other with a bit of color on their faces. Rory started to open her mouth as if to correct what she had said, to make it sound less forward.

"You can," Jess said softly and quickly, before walking away so he could keep the moment as it was, without her saying anything to correct it.

* * *

After school, Jess swung them by his place first for a change of clothes before heading to her small hometown of Stars Hollow. When they got to her house she darted inside to change, and then she began giving him the grand walking tour.

It was a small town – the kind he wasn't too sure he would fit into. Everyone seemed to know each other and their business. They were stopped several times just so people could ask Rory how school was, and not in the 'small talk' kind of way. Jess took in the genuine love and concern these people had for her. He understood why when Rory explained the entire town played a hand in raising her when her mother had arrived as a runaway teen with an infant in her arms.

The amount of pressure he usually felt in her aura made more sense. With this many people watching over her, the idea of failure had to seem more daunting. He was personally used to no more than one person at a time having concern for him and what he did, so disappointing someone was somewhat foreign to him. He couldn't begin to fathom having a whole town concerned.

The bookstore boasted a fine collection of rarities and an owner equally knowledgeable in what he had. Jess found himself in a deep discussion with the owner, while Rory listened in with a delighted face. After awhile, her stomach was growling loud enough she had to drag him away. Rory was not one to skip a meal.

"I didn't know if you would like this kind of place," Rory confessed over dinner.

Jess pulled away from his burger for a moment. "The diner?"

They were sitting in a place called Luke's, sitting at the counter while chewing away at their food. It was one of the best burgers he had ever had and couldn't believe it was from some glossed-over town in the middle of nowhere.

She shook her head, loose auburn hair flying. "The whole town. I know it's kind of quirky and not like other places. But it's home for me."

"There's a lot of people who care about you here," he said.

"Yeah. It will be hard to leave them all for college," she sighed. She was dipping a fry in a mixture of salt and pepper before chewing on it a bit sadly.

He gave a shrug, shooting her a teasing smile. "Whelp, can't be a small town princess forever."

"I'm not a princess!" she grumbled, throwing a fry at him.

He raised up a brow in disbelief. "I believe I saw a 'Rory curtain' earlier?"

* * *

Jess was uncomfortable enough he now had more to do for this project than before. He did _not_ need Rory's towering boyfriend looming around, sending death glares at him. _He knows I've been with her all day_ , Jess realized. _He's never been best buddies with me or anything, but he's never given me a look like that._

They had started running their scene – the death of the lovers – when Dean appeared in the doorway of the ballet studio. His face was moody as Rory stopped the scene and ran over to greet him with a kiss and confused smile, asking what he was doing there.

The rest of the group – Jess, Paris, Madeleine, and Louise – listened as Dean stated he wanted to watch them practice. When Rory frowned and mentioned he would be seeing it in a few days, that seemed to only upset him more.

"Don't you want me here?" he frowned. "I saw you showing Jess all over town while I was working. You spent all day with him, so why can't I be here to get you for some of the day too?"

Rory sighed, growing frustrated herself. "You know it's not about not wanting to see you. We're just really strapped for time. Jess had to transfer to our group last minute to replace Tristan and we really need to concentrate." Her brow was furrowed like it usually was when her and Dean were arguing. The usual soft and smooth face contorting with irritation.

Dean didn't seem to notice he was upsetting her. He pressed further. "So _concentrate_. I'm just standing here watching. Trying to support _my girlfriend_." He said the word as if he were reminding her what she was to him. As if it was her role in life. Madeleine and Louise watched with interest, seeming to find this side of the boyfriend extremely attractive.

"Ooh, angry boy-toy," Louise purred, fully inspecting the full height of Dean from where the rest of the group was standing at the back of the studio. "It's kind of sexy he's getting angry."

Jess rolled his eyes, looking up from the play booklet he was working to memorize lines from. He was perched at the edge of the stage, a bit secluded from the rest of them. "What's sexy about someone getting mad and trying to control you?" he muttered. "You're ultimate fantasy to be locked up in a dungeon or something?"

"If he's doing the locking," she grinned.

He rolled his eyes again, going back to the booklet. Eyes skittering above the pages, he watched Rory finally agree to let Dean stay if he promised to be silent. He agreed, they kissed again, and she retreated back to the group looking more worn out than when Paris had been scolding them before.

"Your lover's spat over so soon?" Paris glared, folding her arms across her chest. "Come on, people. No more interruptions! We've got two days and Holden Caulfield over here needs to impress the pants off of me."

"Not interested, Paris," Jess interjected, eyes back to his lines.

The small blonde grabbed him by the collar and dragged him to his starting position. "Shut up and act," she growled. She directed everyone else to their spots as well – a bit more gently – and then began the scene.

Jess didn't put in a profound amount of effort as he recited the lines. It was Shakespeare after all and he had no passion to attempt to make it interesting. But he started to grow uneasy as they neared his moment to kiss Rory. She was peacefully lying on the floor, eyes closed and fingers knit together across her stomach. The idea of the kiss was terrifying. He remembered how that first time he tilted up her chin how the memory raced in his head for days, driving him insane. _I don't need any poison,_ he quipped, _This kiss alone will be kill me. And now with tall, dark, and brooding over there watching, even if I don't die from touching Rory, he'll certainly make sure I do soon after._

" _O true apothecary, thy drugs are quick_ ," he read on, barely above a monotone, tossing the makeshift 'poison' bottle aside, " _Thus with a kiss, I die."_ He was kneeling next to Rory, one hand softly brushing at her hair. His blood ran cold as he leaned close, starting to feel the shallow breaths she was making tickling his skin. Snapping his head up, he stared at Paris and deadpanned, "Then I kiss her, right?"

Paris's eyes were slits. " _Yes!_ So why _aren't_ you?"

Jess motioned over at Dean, as if it were obvious. "I'm sorry, do _you_ want to be the one to kiss her while this guy is gnashing his teeth at you?"

"Hey, I was being perfectly quiet over here," Dean piped in with a scowl. He had surprisingly been silent, but his eyes were angry and his jaw constantly working into a deeper frown. He was starting to become good competition for Paris as far as scowling went.

Jess shrugged, remaining playful and aloof. "You're death glare is making it perfectly clear I'm done for if I kiss your _number one gal_."

Rory sighed, getting up. "Jess, stop," she warned, her eyes serious. "Dean knows this is for school and doesn't mean anything. Right, Dean?"

Dean gave an extremely unwilling 'yeah'.

She whipped her attention to Jess. "He knows it's for school. So just kiss me so we can get an A."

He had a comeback for her, but could see how tired she seemed over the situation. _Wonder if their little argument earlier has been going on longer than just that,_ Jess wondered. Giving up, he turned to Paris. "Let's just save it for the actual play. It's not like you can mess up a kiss. And that way, Dean's happy, you're happy."

"I don't care what Dean wants," Paris interrupted. "It's not his grade at stake here!"

Madeleine was frowning at her script. "It doesn't even exactly say he kisses her in the play. I mean, I know he says 'thus with a kiss' but there's no stage direction until Juliet comes up. So we could just-"

"Hundreds of directors have made the choice to do a kiss there so we're doing it too!" Paris shouted, waving her script around. "Kisses get A's!"

Jess smirked. "Guess we know how Paris is getting into Harvard."

Paris shot him an even scarier look than Dean had been giving him. "Fine. _Don't_ kiss her for practice. But if you don't do it on Friday, that lovesick puppy over there will be the least of your concerns."

As they all packed up everything later once practice was declared satisfactory by Paris, Jess stuck his hands in her pockets and walked over to Dean. He was starting to not like the guy too much, but Rory was always quick to defend him and Jess thought it was maybe best to keep the peace. Dean was keeping his eyes on Rory, who was deep in conversation with Paris. He didn't shift to show if he noticed Jess suddenly near him or not.

"Hey," Jess began, staring up at the boyfriend. He scratched at the back of his neck, not sure how to address the situation now that he was here. "Look, I was just messing around earlier. Trying to make light of an awkward situation."

"Stay away from her."

Jess narrowed his eyes. "Excuse me?"

"After this project," Dean continued, eyes darkening as he finally looked down at him, "I don't want you hanging out with her anymore. I work over at the grocery store. You think I didn't see you skipping around all over the town square with her today?"

"I don't recall any skipping-"

"There's something going on here," he went on angrily. His hands balled up into fists at his sides. The knuckles whitened. "You think I don't notice how much she mentions you or how you look at her in that way?"

"In what way?" Jess growled, ready to deny anything Dean brought up.

Dean took a step closer and towered over him with a bitter expression on his face. "Your study sessions are done, school's almost done, and you know who she'll spend the summer with after her trip? _Me_." The words were spat out as if they were toxic. "I _make_ her happy, and I've _been_ making her happy since before you came along."

Jess took note of the words Dean chose to emphasize. "Why can't other people make her happy too? Seems to me this whole town cares about that."

Dean glowered. "You're not part of this town. You don't get to care about it."

"Do you hear how damn possessive you sound?" Jess scoffed. "She's her own person."

"She's my girlfriend. So again – stay away from her." Dean walked over to Rory, grabbed her by the arm and started to lead her out of the studio. Jess watched until they were out of sight, his eyes dark with concern.

* * *

 **A/N: So, I've obviously adjusted some canon timeline events, but some things I wanted to keep in just at different times. And Dean getting stupid over the school assignment was such a big starting point for seeing how jealous and controlling he can be in the show, so I wanted to have it in this. Also, gives a reason to start sparking some serious Literati ;)**


	9. Chapter 9

_There's never been an audience when I've_ _pictured kissing her,_ he grumbled to himself, a hand reaching to touch her face. He brushed at her skin tenderly, taking in how serene and delicate she looked, wishing her could keep the moment going longer. The hundreds of eyes staring at them, however, made him in the same breath want it over with.

It was their group's turn to present their performance on stage in front of an audience of classmates, parents, and teachers. They were nearing the end of their scene, and Jess had lingered on lines as long as he dared to – while catching glimpses of Paris's piercing eyes from side stage – in efforts to still his heart before the line he knew was going to cause trouble for him later.

He hadn't told Rory about Dean's confrontation after practice a few days before. Whether she would believe him or not, Jess knew she needed to notice it for herself. _If he was_ that _upset from me not kissing her up until now…_ He had a feeling after this scene, the possessive and jealous behavior of Dean would become more apparent. Maybe she would finally end things with Dean, taking a huge burden off her back.

Jess couldn't move his eyes from her, getting lost in thought about how he had slowly come to care for her. His breath caught in his throat as he kept taking in her long lashes and soft mouth. " _Thus with a kiss,"_ he recited softly, gaining some bravery, " _I die._ "

He placed his mouth on hers, expecting to be able to remove it just as quickly. But her lips were softer than he had imagined and he felt himself drowning in them, only wanting to go deeper. He pressed his mouth against her even more, his skin prickling with shivers. Suddenly aware of the audience again, he rolled away from her and feigned death, heart hammering loud enough he was sure the mic attached to him was picking it up.

 _She's going to ask about that_ , he groaned. Her knew her well enough by now to know she was already planning out a million questions for him. He had lingered a moment too long for a kiss that wasn't even scripted in the stage directions. There had been too much meaning in that kiss for a high school project. His dread built as he pictured how Dean probably saw it too. _He definitely is going to know I'm interested in her now. I may have dodged him a bit before, but he knows now._

And then, his world of thoughts left him. He had been so lost in thinking that he had messed up, giving too long of a kiss, when Rory finished reciting her line and was suddenly kissing him. It was delicate and sweet, but it ended all too quickly. His stomach tightened. She had kept her kiss to the point, appropriate for the play.

The lights went down, the curtain pulled shut after their scene and Jess was already stomping away to sneak a cigarette in the restroom. Paris was at his side in an instant while he fumbled in his pocket for his lighter, cigarette already wedged between his lips.

"You could've put a little more effort in your 'thee's and 'thou's but you surprisingly sold me on that kiss," she remarked. She kept better pace with him than Rory usually did, but he wasn't surprised. This was a girl constantly on the move. "I still think we should have actually done it during the practices." She gave a bit of a scoff. "I wonder how Lurch feels about it now that he finally had to see it happen."

"Lurch, huh?" Jess smirked. He hadn't stopped to think he might not be the only one picking up on Dean's uncomfortable demeanor.

She shrugged casually, as if it were obvious enough that everyone saw it. "He's always looming over her. Seems more like a bodyguard or a hitman to me than an actual boyfriend." She paused a moment before rolling her eyes. "But Rory seems to think he's the bee's knees so I guess it's charming to her. Anyway, I think for now it's safe to assume our grade will be fine. You may have saved us with that kiss."

He reddened, darting his eyes away. "Don't know what you mean."

"Oh, come on, even _I_ felt that kiss," she huffed, giving him a knowing grin. _She looks like the Cheshire cat_ , he thought in annoyance. Paris raised up her open palms as if to wash her hands of the topic. "Look, I don't care what weird love triangle situation you're in, I just want my A on the assignment."

"No triangles here, just tried getting you your stupid A," he snapped, walking faster as he finally spotted the door to the restroom. He refused to look back at her. "Leave me alone."

He holed himself up in there for awhile. Mr. Medina was probably giving some sort of closing 'thank you' speech and then there would be mingling, so he knew he wasn't going to be missed. Three cigarettes later, he put on a brave enough face and walked out. Nothing could have prepared him for the display he was witnessing in the hall. It was obvious Dean was going to be upset over the kiss no matter what, that had been certain since rehearsing started. The way he was belittling Rory was more than expected.

"Oh, here he comes now," Dean said with mock happiness when he caught sight of Jess, who was cautiously approaching the couple arguing in front of him. "You wanna explain to me what you're doing kissing _my_ girlfriend like that?"

Jess rolled his eyes, pocketing his cigarettes. "Chill, man. It was a school assignment."

"Which you totally took advantage of."

Jess's expression darkened. He was getting sick already of everyone pointing out the stupid kiss he hadn't meant to linger on. "Hey, I didn't do anything that I wasn't supposed to do, okay?" he defended. "I don't know why everyone is obsessing over this. She kissed me too, idiot. _Also_ for the assignment."

The boyfriend jutted out his jaw. "Your kiss was _way_ different from hers."

"Dean, _stop_ ," Rory stepped in, eyes pleading. "You're exaggerating how long it was. I don't even remember it – it was over so quick! I don't know why you're so upset!"

Jess couldn't deny the pang he felt to hear that. Regardless if she meant it or was only trying to calm everything down, it wasn't something he was excited to hear. "Exactly," he said, nodding to agree with her. "And now I'll never have to kiss her again. It's back to being your job. I quit."

He quickly went to the changing room, eager to get back into normal clothes and get away from the blue eyes watching after him.

* * *

 _She called me_ , he thought as he heard her voice over the phone. _Just an hour ago her boyfriend was yelling at her about me and now she's called me._

He had gotten home not long ago and was already in the middle of lighting yet another cigarette, cursing himself repeatedly for the kiss, when the phone rang. The call was a surprise. In anything, he figured she'd be spending the rest of the night tending to Dean.

"Rory." He tried to sound indifferent. "Hey."

"Hey," she said tiredly. There was an obvious strain in her voice. "Look, I'm sorry about all that earlier. Dean's usually really nice. He was mad back when Tristan was going to be Romeo, too. He wasn't exactly skipping in circles when I told him it got changed to you."

He made a face. "Why is it worse because it switched to me?"

She was quiet a moment, and wishfully he thought he heard her voice catch, as if she started to reply but had to stop her initial response. "I guess just since we talk a lot and hang out." She sighed. "I don't know. I promise it'll be fine now that this dumb project is over."

He didn't agree. "He doesn't seem to like us being friends."

"Dean's just having a bad week." _She's always so quick to stick up for him. What the hell has he done to earn this kind of loyalty?_

"Rory, he obviously does _not_ want us hanging out. So what will you tell him when we do?"

Another sigh, more withered. "I don't know."

"So we probably shouldn't hang out."

"No!" she said quickly. Her voice grew a bit of an edge. "Don't say that. Just because he's my boyfriend doesn't mean he can tell me what to do."

"Seems to be what he's doing."

"Well, it's not." Her tone was now hard. "I just don't think I should mention your name around him for a bit. Make it easier. Plus, school will be out for summer next week. I'll get back from Washington and spend some time with him and by then we'll be fine and it won't matter if I bring you up."

Jess was quiet. He wondered how she managed to always be so optimistic. It was something he admired, but sometimes couldn't stand. Sometimes things were just messy and didn't turn out right. Over the years, he had learned that well and that it was better not to expect things to work out perfectly.

"We were going to hang out before you left," he finally said. "You still think it's a good idea?"

"It's fine," she assured him quickly. "I'll say I have running around to do."

"Huh. Rory Gilmore is going to be sneaking around with me behind Lurch's back."

"It's not sneaking if we aren't doing anything wrong!" she exclaimed. "And did you get that from Paris?"

He smirked. "Might've borrowed it."

"Well return it," she giggled. "I don't need _both_ of you coming up with weird nicknames for him. But anyway, I just wanted to call and apologize and make sure we were okay."

He chewed the inside of his cheek for a moment, picturing her sitting on her bed with the phone next to her face, her eyes worried at the thought they might be having some kind of fight. The idea of her being worried to be fighting with him made him feel a bit lighter inside after the night's events. He took in a breath. "We're okay."

She smiled. "Okay."

* * *

 **A/N: And let the Literati games begin...**


	10. Chapter 10

It was the day before Rory was leaving for Washington.

Jess had never known anyone who made a schedule for packing, but Rory never ceased to amaze him with how much structure she had to her life. At first he wondered if it was more of her whole picture perfect lifestyle, but when she excitedly talked about accomplishing things off her list as the trip grew closer, he realized some parts of her organized personality were solely for her. That relieved him, knowing she did some things for herself and not just because she was _supposed_ to.

It was the first time alone they would be spending together since the play and he wasn't sure how to feel about it. He certainly didn't know how _she_ felt about it. They hadn't discussed it beyond both rolling their eyes when Paris wiggled her brows at them when they received their A. He was perfectly fine not bringing it up to Rory, but the constant dread of wondering if she was going to at some point was driving him a bit crazy.

After the blow up from Dean, Jess and Rory had to end their final week of after school walks to the parking lot. Every day right as Rory appeared in the courtyard, Dean was waiting by the main gate of the school. She would walk up to him with a smile, give him a kiss, and they would drive off. Jess would witness it from a far, silently hating the feeling building in his chest. It wasn't like he had made some confession to Rory or kissed her on his own terms – much as he wanted to. There wasn't – on the surface anyway - any reason for her boyfriend to be so angst the friendship.

But finally the day arrive, the day Jess had Rory all to himself. He met her at the bus stop, grinning wide and not even bothering to hide it. The fact she was using her last day in Connecticut to spend with him over anyone else was something he definitely hadn't let go unnoticed. It meant something, to some extent.

She bounded off the bus with a grin to match his. "Our clandestine adventure begins!" she cheered, wrapping her arms around him in a hug.

He hadn't expected the contact and felt his heart beating wildly as he moved to hug her back. She was already out of his reach before he could, and he quickly dropped his arms back to his sides. He motioned for her to follow him and they began walking. The weather had been beautiful, so he had wanted to walk to pick her up rather than drive. He wasn't much for driving anyway if he could help it.

"Clandestine, huh?" he smirked, as the bus stop grew further and further behind them. "What did you end up telling the jealous lover?"

She shifted her eyes a bit. "I said I had things to do and I'd be running around doing last minute things before I leave. I didn't like having to half-lie to him, but you're my friend and I wanted to see you."

"Well I _am_ I thing you could _do_ , so I suppose you didn't lie," he said huskily, then laughed as she blushed furiously and gave him a light swat. He couldn't help himself. He was in too good of a mood and shamelessly had to see her get shy on him.

"Oh, cut it out!" She jabbed a finger at his chest. "You say things like that on purpose to make me get embarrassed!"

He grinned. _She's on to me._ "That I do. It's payback."

She frowned, growing confused. "Payback? For what?"

He caught himself, realizing he had been starting to admit she made him redden and feel embarrassed every time she was near; that he loved making her blush knowing he was causing it. Feeling a flush of his own start to rise, he thought up something to say but couldn't. Luckily, her phone buzzed with a text and she pull it out to read it.

They walked in silence for a moment as she read, gave a quiet groan, and replied to the message before sticking her phone deep into her bag instead of back in her pocket. "So," she said, turning her focus back on him, "What are we going to do for our big cloak and dagger day?"

He turned to her, eyes flashing mischievously. "I want to show you a place. We're almost there."

When they stopped in front of the yellow house, he felt his breath catch. His expression darkened as he stared at it, trying to adjust to the fact he was acknowledging it head on. Rory watched him silently, uncertainty in her eyes.

Voiding himself of the dark thoughts, he faced her with a sad grin. "Sorry. It's kind of hard to be here."

The pieces clicked in her head. "It's Nathan's house," she said quietly, understanding.

"Yeah." He took in a deep breath, looking back to the front door. "Let's go in."

"Go in?" she frowned. "You have a key?"

Pulling out his keyring, he picked the right one and flashed it at her, the sun glinting off the metal, before he walked hastily up to the door. Rory stumbled after him, still at a loss.

"You still have a key? Why? Are we allowed to be doing this?" she was a flurry of questions. They were on the porch in front of the door now. She inhaled sharply. "Jess, I know I said clandestine and all thing, but I wasn't thinking we were breaking and entering today."

He unlocked the door, letting it swing itself open, and didn't move for a second. He stared into the house for a long moment before taking a step inside. "We're aren't breaking and entering," he said. "I own it."

She stared at him in disbelief. "You _own_ it?"

"Yeah."

He spun around to face her, as he was now just inside the house, hovering in the doorway and she was still firmly on the porch giving him a confused face. He leaned against the door frame as he gathered his thoughts, figuring out how to explain it so she would stop giving him such a wary look.

"I told you Nathan didn't have kids, right?" he started, fumbling to put the keys back into his pocket. "Well, he left me this place. To fix up and sell or…" He trailed off, hesitant. "Or if Liz's place got repossessed and I didn't have a place to go. Or if Liz was _home_ and I needed a place to go."

The confusion started to lift from her face, but not by much. "Liz? Your mom I'm assuming."

He nodded. "I haven't been in here since he died. I didn't even know it was mine until some lawyer guy showed up." Shoving his hands in his pockets, he glanced over at her shyly. "Just kind of felt like showing you. It's whatever."

It wasn't 'whatever'. He really wanted to share this with her. Sharing about himself with words wasn't easy and made him feel too weak and exposed. Sharing with her by showing felt more personal and was a kind of vulnerability he was okay with.

She smiled. "Okay. Show me."

He led her around, telling stories about the life that had been lived in that house. He showed her the master bedroom and explained Nathan had kept all his books in it and slept in the smallest room in the house; how there had been a very obscure way about how the books were organized in a series of shelves and drawers and boxes. Rory seemed to enjoy that part most, mentioning she herself had given up all her drawer space in favor of space for books.

Jess started to feel happy about being in Nathan's house again. He had been afraid being in it alone would be too hard. The decision to bring Rory made him feel more confident about going in and so far he wasn't regretting his choice.

"I'm glad you brought me there," she said after they left and started heading for the next spot on the agenda. She nudged into him lightheartedly. "I know it's probably hard, but it sounds like he really was there for you."

"He was," Jess grinned. "He was just some old guy who saw a lonely kid and gave him a book. Probably had no idea he'd end up pretty much adopting me."

Rory grew serious. "Did he ever try to? Adopt you, that is. You said you knew him since you were seven."

He was puzzled she would ask that. "I don't think so," he frowned, shaking his head. "It's not like I was a family member's kid or anything. I was just some boy he could share books with."

She didn't seem to agree. "I bet he wanted to. Sounds like you meant a lot to him too."

He shrugged, starting to feel uncomfortable. "Maybe."

He had never given much thought to Nathan being around once it became a habit. Jess still had his freedom to do as he pleased, so it never once felt like Nathan was _intending_ to be a parental figure. The thought started to bother him, so he quickened their pace to their destination.

They end up at the bridge and stayed to read under the warm sunlight. He just wanted to show it to her at first and tell her it was kind of an escape place for him, but she ended up loving the calmness as much as he did so they grabbed a blanket and spread out, settling down to read side by side. She pulled out a book of poetry from her bag and he looked at her stunned as he saw the author's name. As she pulled open to the section she left off at, Rory caught his wild stare and frowned.

"What?"

"Neruda, huh?" he smirked. "Isn't some of that a bit racy for your blushing cheeks? I don't want to glance up from Hemingway every now and then seeing you looking all sun burnt."

She flustered and gave him an irritated scowl. "I thought you didn't like poetry, so how would _you_ know what his poetry is like?"

Jess grabbed the book from her and flipped to a poem he recognized. " _I want to eat the sunbeam flaring in your lovely body_ ," he recited slowly in a gruff voice. He cocked an eyebrow at her with a wicked grin. "I can get behind poetry like that."

"Well, so can I," she declared, snatching her book back.

She was still incredibly red, almost purple as she tried to cover her face with the book – mostly to block her view of him smirking at her. Chuckling to himself, Jess pulled out his own book from his back pocket and they both grew lost in literature as the day moved forward, the sound of the wind in the trees and birds singing as their soundtrack.

He zoned out of his book at one point, thoughts getting lost in a million other things. It was his last bit of time with her for a long time – maybe they should get up and do something a bit more personal before she headed home for the night. The sun was lowering anyway, so they would be forced to leave within thirty minutes as it was. Growing restless, he started to lower his book to ask Rory if she wanted to go eat somewhere, already knowing the answer would be a resounding 'yes'. That was went he noticed she wasn't laying where he last saw her.

It had been so gradual, so delicate, he hadn't felt it happen, but Rory was resting her head on the lower half of his stomach, her long soft hair spread across his dark shirt and part of the blanket underneath them. His breath caught in his throat as he watched her reading, the sun catching in her hair, bringing out all those hues he had come to admire.

He didn't want to move. This felt so intimate and right, but if he moved she would be startled out of her reading, realize how she was being cushioned by his body, and become embarrassed in a way he didn't want. They might never have a moment like this again; it made him want to reach out and cup her face, bringing her closer and take advantage of this proximity. He had watched her mouth for half a year now – watched it as she laughed, as she carefully examined text while silently mouthing the words to herself, as she debated with him over music and literature. All the watching made him only want to kiss her more, to see if they had some kind of physical connection to rival their mental one.

"Jess?"

Her soft voice pulled his eyes away from her mouth and he noticed she was watching him watch her. She had leaned up off of his stomach but was still seated somewhat closely to him, resting on one elbow. Embarrassed, he cleared his throat and made a big show of stretching his arms above his head and yawning. Anything to distract from the awkwardness. He crossed his arms behind his head and looked at the sky above them, eager to look anywhere but at her until the heat left his face. When he felt brave enough that she must have moved back to her book, he gave a quick peak, only to find she had abandoned her book beside his.

His watched in a daze, propped up on his elbows, as she stared at the two inch strip of stomach that was now bare from when he had stretched. The curve of his hip bone was out, a raised hill beside the smooth flat skin beside it. Why this had her attention was beyond him. She and Dean had been together awhile. Surely they'd done something enough to see more of his skin than others saw every day. She at least had to have seen him with him shirt off.

But her eyes were wide and curious as they took in the exposed flesh. He wondered if she was thinking about the line he had read to her, noticing the glow casting over both of them from the setting sun. To his surprise, she timidly reached out almost absentmindedly and slowly moved her left hand over to the skin. Her fingers gingerly found contact as she stroked a soft, very faint, line on the crevice of his hip. Instinctively, he held his breath. The feeling of her touch somewhere so sensitive was galvanizing. He swallowed, suddenly finding his throat dry as she continued tracing faint patterns on his stomach. Uncontrollably, his jeans tightened.

 _Shit._ She was sure to have felt it. Her forearm was resting right across the fly of his jeans while she traced. The movement shifted her forearm upward slightly and her eyes promptly moved to meet his. Realization that she was turning him on appeared on her face and a seductive smile crept over her mouth. She kept her fingers where they were, still drawing on his skin. A bit more pressure in the touch suddenly went at the crevice and he found himself letting out a frustrated groan at the unanticipated force. He shot her a beseeching look.

Understanding, Rory began to crawl steadily up his body, hovering just inches above him. Her eyes were different. She seemed to still be in an absentminded curiosity, but there was a growing hunger there as well. He heart quickened. _She's enjoying this._

He had no idea what was going to happen once she reached his face. The thousands of times he had pictured getting to kiss her for real, to touch her without holding himself back, it had never been a situation like this one. Now that it was happening, it was everything he had wished for and was already disregarding previous imagery.

His own hand came up, waiting for her to get close enough. Rory's face reached his, and her quick breaths tickled at his mouth. His fingers caressed along her jaw, cupping around her face naturally. Jess didn't know what she was reading in his expression but her smile deepened, her eyes softening.

Her tongue peeked out a tiny bit and ran over her mouth to wet it, right as her phone chimed from a few feet away. Suddenly pulled back into reality, her eyes widened and she blinked several times as she got a hold of herself. She flitted her eyes, taking in the position she was in and reddened, getting to her feet to answer her phone.

 _This feels familiar_ , Jess groaned as he felt the bulge in his pants tighten in frustration. He leaned over to dip his hands in the water, splashing his face a few times to calm himself. It was the closest to a cold shower he was going to get.

Rory was frantically shoving her things into her bag. "That was Dean," she sputtered. "He wants to see me for dinner. I should go now. It'll be easier if I just go now."

He watched her grab her books in a whirlwind. Their day together couldn't end like this. The awkwardness needed to be broken. "You still going to write me while you're gone?" he asked, getting up.

She was distracted still, mind clearly spinning. "I could."

He blinked. "You could."

"I _will_ ," she said, more sure, as the last of her things were packed.

She quickly started to leave the bridge, but he reached out and caught her softly by the wrist. Her eyes looked up at him, nervous, ashamed, embarrassed… several things she had been the opposite of just minutes before.

"Thanks for… reading with me," he said with a slow smirk at the last bit.

She crimsoned, staring off into the lake as she stumbled to speak. "Well, I… you know, I was reading all that poetry and just kind of got caught up in it and… and well, clearly I got so caught up I thought I was with Dean for a second so I got carried away!"

"You thought you were with Dean," he repeated.

She nodded quickly. "Yes. My boyfriend."

Jess couldn't help himself. He leaned a bit closer so their foreheads were nearly touching and gave her a knowing expression. "I suppose Dean and I do look very similar. I could understand the confusion."

She licked her lips nervously. "That's..."

He continued, pretending to ponder thoughtfully. "No, it makes sense. We're _clearly_ the same height, same hair color too, I think? We both rock that Chilton uniform _very_ well might I add."

"Jess," she said with warning in his voice.

He felt brave. "I suppose we probably even _kiss_ the same."

She rolled her eyes at that one. "We kissed for a play, that's hardly a basis to compare kissing with."

"I could give you a basis," he grinned, still riding that sudden bravery. She flushed even more and he knew he had to stop himself or he would end up trying to get back to where they were earlier. He held up his hands in surrender, taking a few steps back from her. "I'm joking, I'm joking. Come on, I'll walk you to the bus stop."

She shook her head, still seeming dazed and unsure of what had happened. "That's okay. I really need to hurry so I'll probably just run." Taking off, she was at the start of the bridge in no time. Flashing her head back for a moment, she called back, "Have a good summer, Jess!" and then was out of his sight.

 _So close_ , he thought as he stayed perfectly still, afraid if he moved he would find himself waking from a dream.


	11. Chapter 11

She never wrote.

She never called.

 _It has to be because of the bridge_ , he told himself as the weeks dragged on and there was no contact. He felt like an idiot, waiting around the house – a rarity – to check the mail and listen for the phone to ring. _I've never been this guy. I hate these kinds of guys._ Rory was a weakness though. A weakness he was beginning to regret allowing to happen.

To say he was hurt was an understatement. They had never had a moment like this in their friendship – an awkwardness stretching this long. Even ever since their first few days getting to know each other, there hadn't been a longer stretch of time than a day or two they hadn't spoken.

 _So why is she doing this now?_ he thought bitterly. _How aren't we at a point we can talk about what happened so we can just move past it and forget it?_ He knew what was happening. She was embarrassed and afraid and wanted to stick tightly to her precious perfect boyfriend. As much as it hurt, Jess was used to his quiet pining for her by now he didn't expect her to drop everything for him just because of one afternoon she showed actual interest in him. She couldn't really have thought he was Dean that day. That smile she gave him right before her phone went off was a smile she saved only for him. Any smile Dean got was small, soft, and reserved. Perfect and expected. What Jess got was wide and warm. Something he could drown in thought over.

Being left alone gave him time to do something he hadn't planned to do. He found himself giving a shot at writing. There were certainly enough feelings bubbling inside of him. If he could channel some of the bitterness and the pain perhaps he could start to feel some relief or closure.

The biggest thing weighing on his mind though was, _Will I be forgotten once she comes back?_ Would their dynamic change or would she go on ignoring him? He didn't leave much room for fear in his life, but this thought was slowly approaching something close to it.

* * *

The summer was coming to an end in a matter of weeks and he had grown bored of waiting.

She wasn't the person he was picturing, but with the lights low and his eyes tightly shut it didn't seem to matter. He had called up a girl, Shane, that used to flirt with him at his old school when he bothered to show up for class. She was more than happy to see him after such a long time. Clearly the crush was still there. After walking around sharing a cigarette, he realized she didn't have much to offer conversation-wise. Jess took her back to his house, deciding she at least could distract him in other ways. He opened some beers and turned on the tv, but everything was soon ignored as Shane wasted no time getting to the point.

He felt himself react to her sliding her hands down his back, her tongue in his mouth, but the feelings weren't the shock he had felt almost two months ago. _Not everything feels like that,_ he told himself. _And that wasn't even a kiss. It wasn't anything. It was a fluke._ Rory had just caught him off-guard by touching him when he wasn't expecting it. Surely if Shane did the same thing, he would be just as unhinged.

At the passing thought of her name, he pictured again the curiosity and bit of hunger that had grown in Rory's eyes that day on the bridge. Imagining her fingers touching him and those lusting eyes made him grow harder. He pushed against the girl beneath him, grinding his body and his mouth into hers, stifling drawn out moans from her throat.

And then the phone finally rang.

He leaped off the couch and several feet away, staring in wide-eyed terror at the phone as it let out a repeating shrill. His heart hammered wildly, threatening to break through his ribs. _Why now? Why when I finally try to stop thinking about you?_ Nobody else ever called. It had to be her.

Sure enough, it was.

The answering machine clicked on and her soft, shaky voice filled the room. "Um, hey, Jess. It's… Rory. Which you probably know already. From the number, I mean." A long pause. "So I'm back from Washington. I'm sure you figured that out by now. Um, been back about a week or two. Paris was as expected. You seriously won't believe some of the things I went through rooming with her." Another pause. "My mom hasn't been letting me out of her sight, claiming pretty much all my free time to make up for me being gone." Another pause. "A-and Dean. I'm of course spending time with Dean. Um, anyway. I hope… you're good. And… staying… hydrated? Um, okay. This was Rory Gilmore." Click.

He blinked as he listened to the most rambling machine message he had ever heard in all of his life. It was clear she knew she messed up by cutting off contact to him. _I could have done without the Dean update_ , he narrowed his eyes bitterly. The parts where she was clearly at a loss for words were cute and made him remember what about her got to him so much. But it still had been eight weeks.

"Girlfriend?" Shane asked with a raised brow, breaking the silence.

He grunted. "As if."

"Why didn't you answer?"

"You're here."

"You _sure_ she's not a girlfriend?"

"I think I'd have some kind of knowledge on the situation, yeah."

Shane gave a sheepish smile. She was still sprawled across the couch, shirt a mess and half off her body. "I'm just saying, you flew across the room before even knowing it was gonna be her."

Jess rolled his eyes. "More that I was _startled_."

"You don't seem mousy enough for that."

"Whatever. Can we get back to what we were doing?"

He was back on top of her in seconds, trying to work back to the intensity they had been at before the phone rang. His mouth felt full of cotton and his pants had more give than before, showing no signs of getting tighter. Angrily, he pulled away from her and back to the other side of the couch.

"Dammit," he hissed, slamming a fist on the table. He reached for his beer and finished it in one gulp. Wiping his mouth with the back of his hand, he rests his arms on his knees, refusing to look at Shane. "You should probably go."

She gathered her jacket quietly. "If you ever get over this little number that girl's pulled on you," she called from the open doorway, "Call me again."

The door was shut and he was back to being alone. He grabbed another beer before going downstairs into his study area and then wrote angrily until he passed out.

* * *

 **A/N: Great feedback from you guys as always! A few people are starting to ask if Luke is going to show up. I hadn't planned on it originally, but I'm starting to see a good place I can put him. So we shall see :)**

 **As far as the timeline of the story, it began spring of Rory's junior year, and now it's summer. Her and Dean have been together awhile, so my story is more of a season two feel I suppose.**

 **So we're starting to approach a major part in my story idea. I hope you all continue to enjoy where I take it. As much as I love reading M rated stuff, nothing in this story will reach that. I'll have some scenes that are nearing that but nothing will get explicit.**

 **Michelle - I agree, ASP kind of dropped her characters. The revival felt too dark to me. Emily was amazing, but Rory and Lorelai were just... so different. Way too selfish, more than they usually can be. I wouldn't mind taking a crack at writing an older Rory and Jess, revival version or not, I just am not sure what I would do with that yet, so if there are ideas, I'm happy to hold on to them until I finish this one.**


	12. Chapter 12

It stormed the rest of the week, matching his mood.

By Saturday it was still overcast, but dry enough to venture down to the bridge to do some writing. He was sick of his house, sick of torturing himself in solitude. As he sat on the edge of the bridge, feeling the slight chill of the oncoming storm winds prickle his skin, the writing came all at once.

His writing style was very raw he found, as he had slowly been finding his voice over the weeks. The descriptions felt dark and rough, the emotions intimidating and more open than he was used to being. It was the kind of thing he wouldn't want anyone to see and almost dreaded putting into words in case someone _should_ find it. But it was new and he was enjoying getting to explore this outlet.

It wasn't really a _story_ as there was no real structure. He just kept picking up the notebook every day and seemed to have a flow of paragraphs emerge from him the instant the book was open. It was different from his margin writing. That was _entirely_ different. He wasn't sure if any of his free-writing was connecting or making sense, but it didn't matter. It was his and his alone to see.

 _I've filled up a lot of this already_ , he realized with amazement when he finally set down the pen a bit later. It had only been a little over a month and the book only had about a quarter of blank space left. The idea of completing the book was exciting, almost a challenge; the fact he would have finished something so new to him in a short time, even if it wasn't coherent. He took a bit of pride in that.

As a few light drops of rain dotted the pages, he resolved it was time to leave before his hard work got ruined. His heart came to a full stop as he suddenly felt the vibrations of footsteps on the bridge, the wood creaking softly under the weight. His face fell, not needing to turn to see who it was. Not many people knew about this place, but _she_ sure did. The steps stopped beside him, but she didn't make to sit down. He set his notebook next to him and stared ahead into the water wordlessly. _If she came here to talk, she better damn well talk_ , he thought.

"Is that a notebook? Are you writing?"

It was an icebreaker. Her voice was enthusiastic, almost prideful. It made sense; she _had_ been the one to put the idea of trying to write in his head in the first place. Had the circumstances been different, he gladly would've humored a conversation about how it felt so natural to him to be putting thoughts into words every day.

He gave a stifled, "Yeah."

"Oh my god, Jess!" she cheered, excitement growing. "You have to let me read it! I can't wait to see what you've written! And to know what you write about!"

Jess forced himself to slowly look up at her, meeting her with hard eyes. Her hair was tossing in the wind, her fingers softly pushing some strands off her face so she could see him. Her smile fell as she read his mood.

"Actually," he said bitingly, "I don't think you'd care for some of what I have to say."

She paled, breaking the eye contact to shamefully concentrate on the wood blanks beneath her. He kept this side of him mostly a stranger to her; something she would sometimes witness him use on others when he bothered to acknowledge anyone else, but she had never been the victim of it. Before it would have crushed him to see her look so defeated, and maybe part of him, on instinct, felt a pang of that now. But he had grown increasingly angry over their time apart and was not about to act like they were still fast friends.

"I called you on Tuesday," she said after a minute.

He grunted. "So you did. Finally."

The drops of rain were falling more frequently, but still weren't hard or fast enough to ruin his writing. Getting to his feet, he collected his notebook and stared her down, allowing his dark eyes to fully expose his hurt. She noticed his pain and anger, heart ache in her eyes knowing she caused it. Unable to look at her a second longer, Jess turned to walk away. Before he even made a first step, Rory's arms were closing around him tightly in a captive hug, keeping him from leaving.

"I mess up – I know," she blurted out, burying her face in his chest. "I… I don't know why I didn't write. I started to – I started _so_ many letters! But everything felt weird and I didn't know what to do or send and more time passed and I knew at that point I had messed up and that you probably hated me."

He was frozen, unsure how to respond at first. Instinct made him want to hold her back, but he couldn't just yet. Her apology was something he had longed for, but had long known any answer wouldn't feel good enough to him. He knew the answer he wanted, but was too cowardly to try to get it.

"Rory, you really hurt me," he finally said, still remaining tense in her arms. She pulled away from his chest to meet his gaze. Her eyes were shaking and serious, knowing she deserved whatever he said. "You're the only person I regularly talk to, that I consider a friend. It was really shitty to have you just… _gone_ all of the sudden." _Like with Nathan._

He didn't say the last part, but he saw her connect the parallel. She bit her lip and lowered her eyes. "I didn't even think of… of how that must feel. And to go through that a second time." She stopped, bringing her palms up to her temples. "You thought I wasn't going to ever talk to you again. That you lost me."

He took a step away from her, uneasy with the proximity. "Can you blame me?"

"No. It was stupid of me." She took a deep breath. "Jess, I'm used to things staying the same. My closeness with my mom, my relationship with Dean, my dream to go to Harvard. That's just how things are. The _same_. And… it feels like ever since I met you and started talking with you and reading your notes in your books, I kind of… no, forget it."

She walked off a few feet, staring frustratedly out at the water. He couldn't let her stop there. Walking up beside her, he jammed his hands in his pockets. He wanted to understand.

"No, tell me."

Weary, she gave him a torn expression. "You're just… so different," she gave in. Her tone was one of interest mixed with frustration. "Kind of… unpredictable. Your life feels so fluid and moving, and sometimes I just kind of wonder what that's like. To take more chances or just let things happen or whatever."

He frowned. "Why can't you do that now?"

"Because I _like_ stable. It's always worked for me. It feels safe. It's… right." She gave him a knowing look, brows raising. "I mean, look how I reacted last time I saw you and I took a risk. The second I got snapped out of it I freaked out and now here we are months later and I've been avoiding you."

He smirked slowly. "Could've sworn you said thought I was Dean that day."

She reddened, suddenly backtracking. "Y-yeah, right. I did say that. Dean. Not… you. But… Dean and I don't have moments like that, that are different and unpredictable. So, all of this has just cemented to me things should… stay the same. It's better if they stay the same. When things stay the same I don't become a jerk who ignores you."

Whether or not she meant it wasn't the point. She wanted their friendship how it had been. She was wanting to forget the last time they had been on that bridge together. She wanted to go back to feeling secure in how things were.

"If that's what you think is best," he said after a moment.

"I do," she said slowly, thought he wasn't sure if she sounded completely behind that statement. She looked up nervously. "I'm sorry. I really am. Do you forgive me?"

There was a drawn out silence. He got a bit harsher in his tone as his eyes flashed at her, reflecting the hurt that still lingered even after the apology. "Just… don't do that to me again. Either tell me what's going on, or don't come back like this expecting me to forgive it a second time. Okay?"

She nodded. "Okay. You're right. I told you once that I would be here for you if you ever felt alone, and I royally messed up. I won't let that happen again."

* * *

And so far she hadn't.

While it was still a struggle to forget the pain he had spent the better part of the summer feeling, he honestly _did_ forgive her. Rory may not have handled things ideally, but she had been genuine in her apology.

The Dean situation seemed to only be straining more and more. He wasn't sure how soon the break up was coming, but Jess knew it was at it's limit. Fall semester had begun and Rory was now vice-president of their senior class, an editor on the paper, volunteering a few times a week after school, and about ten other things Jess couldn't remember, all in efforts to keep padding out her transcript for Harvard. When she wasn't working on one of those things, she seemed to be doing her best to keep Dean in a good mood.

There was also the whole college quickly approaching dilemma. Rory was now applying to a few other schools as backups. Why she hadn't wanted to for such a long time and thought Harvard was the only option was beyond him, but it seemed her grandparents had gotten her thinking over the last year that it was smarter to do. So now, it was very open-ended where Rory might end up after they graduated and Jess didn't want to begin to think of analyzing how their dynamic would change.

They were discussing college and essay writing at lunch one day, as application deadlines were almost there. Paris had joined them, always eager to pick apart other people's strategies. She had been grilling Rory for the last twenty minutes before turning her attention to him.

"So," Paris said, raising a brow. "Speak up, Caulfield. What's the plan for you?"

"Finishing this book in peace," he said, flipping the page. He had been listening in bits to their conversation, but since it was mostly things he had heard a millions times before, he had been reading quietly across from them.

"Do they give out degrees for reading a book?" she quipped. "You must have wallpapered a mansion with Master's certificates by now. I'm serious. College. You. Which ones."

"Don't think Kerouac stopped at any," he said casually.

"You want to pull an _On the Road_? Seriously? Sometimes you're such a stereotype for rebellion." She rolled her eyes. "You aren't even going to just apply to some? You're a worthy rival, Mariano. I can't think of any college that would refuse you."

"While I'm flattered, you may have forgotten I'm here on scholarship."

"So is Rory."

He set his book down, finally looking at her. "Her grandparents already offered to pay for any leftover costs after the dozens of scholarships you and I both know she's going to get. Even _if_ I got a scholarship or two, I still wouldn't have the hard cash for the rest."

"Wouldn't it be fun to just see what schools are interested in you?" Rory piped in. "Just to see?"

He looked at her incredulously. "You think writing a bunch of essays just to see how many letters I'll get for schools I can't afford will be _fun_?"

She took a long sip of soda before chewing on her lip thoughtfully. "What if I help you?"

"Help me what?"

"Do your applications and figure out your essays!" she sighed. "I mean, it _was_ my idea. I don't mind helping if you would do it just to humor yourself."

"Do you even have time to help me with something like that?"

"I'll make time. I wasn't supposed to hang out with Dean tonight but I'll message him that I have school stuff to work on." She started to pull out her phone. Jess started to reach out to stop her, but decided against it.

"Okay," he surrendered.

It was getting harder and harder to spend time with her anymore with all her attention focused on application-boosting tasks and occasionally Dean. So if it meant having to scribble out a few essays to have her attention for an evening, he selfishly was okay with that.


	13. Chapter 13

"Wow," she breathed, wide eyes darting over the lines of writing a third time. "You're essays are better than mine. Like, _way_ better."

They were in Rory's kitchen, seated at the tiny dining room table. She had pulled out every college essay prep text she owned, creating a towering skyline of books surrounding them. Jess had just finished writing out a third essay and Rory had been eagerly reading them all for the last few minutes.

He grunted, leaning back in his chair. "No way. You've been pounding away at yours for months. Mine are probably the same as everybody else's. Nobody is going to find them interesting."

She made a show of rolling her eyes. "Well, _I_ find them interesting, so I must be a nobody."

He shook his head. "I can't believe I let you talk me into this."

"Your summer of writing has obviously paid off," she praised, still lost in the essay she was currently staring at. "Paris is right. You're definitely a worthy rival."

"Probably the least mean thing she has ever said."

"She has moments of normalcy."

They had been sitting closely, working hard on the applications for the last few hours. His hand was cramping from the constant grip it had had on his pen. Stretching it out to get some feeling back into it, he turned to Rory.

"So," he said, gaze mischievous. "I wrote all these dumb essays. What's the prize?"

"My company," she replied confidently, still rereading as she sipped her coffee.

He shook his head. "No, no. I'm going to need more than that. I gave up my evening to write these things against my will. I get a prize."

She twisted her mouth around in thought. "What do you want?"

 _Dangerous_ , he thought with a smile. _"_ Hmm. Do I have a time limit to decide?"

"You need to _think_ about what you want your prize to be?" she snickered, raising a brow. "You seemed so sure just now that you earned one I thought you knew what you wanted."

"Let's not get hasty," he said. "I need to take my time and pick the _right_ prize."

"Can't I just take you to get ice cream or something?"

"Three essays are worth more than one ice cream."

" _Three_ ice creams?" she jested. "One ice cream per essay?"

"I'm not lactose intolerant or anything, but I don't think any person can handle that much ice cream at once. Do _you_ want ice cream? You seem to be talking about it an awful lot."

"Hey, schoolwork makes me hungry."

"So… we're going to get ice cream now."

"Sounds like it."

"But I don't want that to be my prize."

She groaned, laying the essay on the table. Her body angled toward him. "Fine. We'll get ice cream. You still have a prize to pick." A pointer finger came up and she tapped him lightly on the nose with it. "But you need to decide soon. I don't want you to suddenly request something twenty years from now when I'm off being a famous journalist."

"What if my prize can only be delivered by you once you're a famous journalist?"

She laughed. "Ah, the long con."

He shrugged and said matter-of-factly, "As they say, _always be networking_."

Leaning across the table, she gave him a devilish smile. "Is that what you were thinking when you rescued me from Tristan way back when? 'Hey, saving this girl is a great networking opportunity'?"

Remaining aloof, he shrugged again. His face was pure innocence. "I might've. Who can say?"

"I don't believe you."

"Then why do _you_ think I did it?" he smirked.

He expected a playful retort, keeping their banter going. Still leaning over the table toward him, she concentrated hard on him, deliberating with herself over how to answer.

"I think you secretly are a gentleman," she finally replied. "Paris may call you Holden Caulfield, but I think there's a sweetness to you."

He shifted, not seeing any benefit to her thinking he was 'nice'. After all, she though _Dean_ was nice. That was the last person he wanted to be in the same category as. "So when you're a journalist," he said quickly, trying to dart the subject, "What parts of the world do you plan to travel to most often? This is important to redeeming my prize."

She laughed, seeing his game. Her hand reached over to give him a playful shove on the shoulder, her blue eyes glimmering in the low kitchen lighting. "Just accept it. You're kind of nice."

Bravely, he caught her hand before she could take it back. His fingers gingerly enveloped hers, his eyes dark and serious. "Only to you really."

She blushed, gently pulling her hand free. "So. Ice cream."

As usual, she was trying to fan out any flames he was trying to ignite. But today, he didn't want to settle for giving up the moment she pulled away. He wanted to feed the fire. "Yeah," he murmured, gazing intensely at her. "Ice cream."

"Should probably go then."

His tone was casual, noncommittal. "We could."

"We could… or?"

"We could… not."

Her face flushed, but she held and matched his consuming stare. "Right. And do what instead?"

A heavy knock on the door stopped his breath, and Rory's face paled at the sound of Dean's voice calling out her name. She shot Jess a panicked look, eyes wide. "You should go," she said quickly, pulling him to his feet. Heading toward the back door, she tugged at his arm frantically. "Go out this way and just wait until he's inside before you get on the main road. Thank god I had you park your car somewhere else in case this happened."

Jess made his weight firm, keeping her from pushing him so easily. "Why?" he countered. "We were doing school stuff. It's not like anything happened."

"It's just easier if you go," she sighed, growing upset. Her chest rose and fell too quickly, too shallow for her to be breathing comfortably. " _Please_. It's just easier."

She was fumbling to unlock the back door with shaky hands. Jess placed a flat palm against the door, holding it closed before she could get it unlocked and shove him out. She looked up at him with fretful eyes. The knocking at the front door continued.

He stared at her questioningly. "Because Dean will get mad?"

She gave a small nod.

Jess scowled. "Rory, you really don't need to take this. That guy-"

The front door opened. Her breathing stopped, as they listened to it close. "Rory? I thought I heard your voice, so I just came inside since you're probably deep in some school book or -" Dean rounded the corner, entering the kitchen. His caramel eyes caught Jess and Rory, huddled by the back door, Jess's eyes full of annoyance and Rory's full of dread.

He glared accusingly at Rory. "Thought you had school work to do," he hissed.

"I did, I helped Jess with his college applications," she explained.

"That's not _your_ school work. That's _his_ thing to deal with."

She sighed. "Dean, I was trying to help him. He wasn't even going to apply anywhere!"

Her boyfriend gave a sarcastic chortle. "Yeah, I'm sure you _really_ bent his arm to spend time with you. Let me guess, he _also_ is applying to Yale, Harvard, Princeton – all the other super smart schools you applied to."

She narrowed her eyes in confusion. "Well, some of those sure, but -"

"I knew it!" Dean spun toward Jess, shoving him hard in the chest. Jess fell backward against the wall, stumbling but still standing. "I told you to back off. She's-"

"- _your_ girlfriend. Yeah, I've heard the speech." Jess rolled his eyes, rolling back his shoulder to ease up the sudden pain he felt. His dark eyes glowered. "But she's also _her_ own person. She wanted to help me, so she helped me. You of all people should know it's hard to refuse her when she's determined about something."

That did nothing to placate Dean. "Oh, I _do_ know it's hard to refuse her," he spat. "Because I love her. So you, a _friend,_ shouldn't be giving in so easily. If you don't have feelings for her, that is."

Jess made a face. "What is this, _Barney_? I'm not here to share my feelings, I just came here to write some damn essays for schools I don't even think I want to go to!" He walked back to the table, gathering his things into his bag.

Surprisingly, Rory went to him first, laying a hand on his shoulder. "Jess," she began, her eyes sad. "You don't have to leave."

"Yes, he does," Dean growled. "Rory, we need to talk about this. I came over to surprise you, take you somewhere for a quick break from your school stuff and I find you here with _him_? You snuck behind my back."

She spun around, her face tightening in defense. "What's the problem, Dean? He's a friend! I've told you that! How many times do I have to tell you that!" Her voice was louder than usual.

Her boyfriend shook his head, throwing his arms up. "Do you know how much I put up with hearing you talk about him? He's more than just a friend, Rory. I even see how you both look at each other."

Her face hardened even more. "Dean, stop it."

"Do you know you've _never_ looked at me that way? You're _my_ girlfriend! We've been together for almost two years and I don't think you've ever once looked at me like that."

Dean was hovering over her, backing her against the wall slowly. Rory's expression was angry and guarded, but her chest was still rapidly fluttering, her hands shaking at her sides. Jess neglected his things and shoved Dean away from her. He knew panic when he saw it. It had been most of his childhood.

"Hey," he shouted, "Just back off. Everyone gets you're mad, but don't take it out on her."

"Jess," she piped in softly. "Maybe you should go."

His eyes went to her, surprised and hurt. "Are you sure that's a good idea?" he gestured to the upset boyfriend off to the side.

Dean scoffed. "I would never hurt her. We're just having a fight."

Jess stared at Rory, concerned. She feebly managed to nod that she would be fine. Her eyes held him for a moment, before she sighed and looked away. It almost seemed like she was embarrassed. This wasn't the embarrassed look he usually loved getting out of her. This felt full of shame.

"Okay," was all he said, as he packed up his bag and left.

* * *

 _Everything is different now,_ she thought in a panic.

She hadn't slept. Her pulse was racing, breaths shallow and fierce. Nothing had felt stable since Dean had stormed out the night before. _He was so angry_. Her chest tightened even more. Anxiety raced throughout her, sending her stomach into an endless fit of nausea. _I have to calm down. I can't keep thinking like this. I have to fix things. Get them back to how they were… but how?_

Her first instinct, as had become habit now, was to call Jess. _Jess._ Her breathing stopped for a moment. Guarded, unpredictable, intelligent Jess. He always had an answer and always had a way to put her at ease.

He also got under her skin. She remembered for a moment the day he asked her what her and Dean talked about. She had raked her brain for days over the question, growing frustrated. What did Jess know? He never saw them together when no one else around. Dean had lots to say about…

She cursed audibly, a rare thing. _Dammit, Jess._

It was just because _he_ was smart and read books she read and listened to music she listened to. So of _course_ she had more to talk about with _him._ Her and Dean had fun too. It was just different fun. It was… predictable. Safe. Usual.

 _Boring._ She shook her head. _No. Not boring. I didn't mean that._ Dean was sweet. He was nice. _Usually. Lately not so much._ Lately being shortly after her and Jess became friends.

And there was was, back in her mind again. _Jess._ In truth, nothing had really been stable since she started at Chilton and met him. She thought about him more, the memory of the bridge flashing to the front of it all. It hadn't been the most sexual thing she'd done, sure. But when her fingers had reached out, nimbly prickling his flesh, she had heard his moan all too clear. Her breathing had hitched and out of instinct, she crawled slowly, lustfully, up his body. Ignoring his chest, his soft, exposed neck. She had looked directly into those dark eyes, reading everything she could from them. Her body had been throbbing at the very idea of him, her mouth eager to finally see what tasting someone her intellectual equal was like. He hadn't touched her intimately at all, but every part of her was ignited by him as if he had.

 _But Dean called. And… saved me. Reliable Dean._

She got out of bed finally once her alarm clock chimed. Her fingers had cautiously been creeping toward her growing heat, but now as reality sunk in, she shrunk away and got up to get back to her realism. Her mother was already seated at the table, reading the newspaper while sipping from a large mug. "You wanna talk about it?" Lorelai asked.

Rory shook her head. Her mother was speaking of Dean. She had to refocus on Dean, not the thought she had just had of Jess and his mouth…

"No. I have a plan though," she said with shaky determination. "To fix things. Everything is going to be fine." She reached into a cabinet to grab some cereal while the coffee brewed.

"I thought everything would be fine too, but then you decided to apply to other schools besides Harvard," Lorelai frowned, carefully setting down the paper. She usually was so fully of energy, but lately she hadn't taken kindly to Rory stepping outside the box. "What's going on with you lately? You don't normally let things get so… loose cannon."

It was true. Lorelai had helped her plan to go to Harvard pretty much since birth. It was half a desire for Lorelai to live vicariously through her daughter, and half knowing Rory was more than smart enough to get in. Lorelai had been extremely angry when her parents had gotten Rory to start considering applying to other schools, even if it was only 'as backups'.

Rory felt the panic rise up again. _I can't fight with mom again. Not today_. "It's nothing. Lots of people apply to backup schools. That's nothing." She tried to sound assuring, but the lack of sleep made her voice somehow sound puffy and out-of-body.

"And Dean?" her mother pressed.

"He just misunderstood. I can fix it."

"And this involves that other boy? From the play?"

"Jess."

"Yeah. Him."

Rory sighed, taking a seat across from her mother at the table, placing her cereal in front of her. For once, she didn't feel all that hungry and just jabbed her spoon laggardly at chunks of wheat puffs. "Dean just doesn't understand we're friends. He'll understand. I have a plan."

"So you keep saying. Can I hear this plan?"

She chewed on her lip. "You might not understand it."

"Try me."

So Rory spilled. And spilled. And _spilled._ She went into more details than she ever had before, laying out every possible scenario and how everything would ultimately lead back to her and Dean getting back together and staying together. _Back to one, singular constant._

Lorelai frowned, her features softening as she considered her daughter's plan. "Sweets. That's… that just won't work how you want it to."

Rory gaped. "Why? I've been up all night thinking it out. It's _flawless_."

"You can't account for how people will react."

"That's why I said that -"

Lorelai shook her head. "Someone's going to get hurt. I don't want it to be you."

"I won't."

 _Yet another reason I need to fix this with Dean._ Lately her mother seemed bothered by Jess's friendship. She may have been less bothered if other things hadn't started to change too. _Everything is becoming too different,_ Rory panicked, feeling brick after brick stack over her chest. _I can only fix so much._

 _I'm drowning._

* * *

 ** _A/N:_ A friend mentioned seeing Rory's POV would be nice and it got me thinking. This was a good place to insert it, while she's having a panic attack, and I hope it gives some insight on her side of things.**

 **I welcome lots of reviews and comments.**


	14. Chapter 14

He woke up with his mind racing.

 _Everything is about to be different somehow_. He just knew. As if on cue, the phone rang and Rory's soft voice greeted him. She sounded empty inside. "Can you meet me at your bridge?"

He met her within the hour and for a long time they sat in silence, except for her occasional gasp for air as she struggled to breathe. Her hand flew up to her chest in desperation, pressuring against it with choking pants. He noticed her eyes racing to focus somewhere, _anywhere_. Softly touching her shoulder, he got her to face him and he held her gaze firmly while she settled her breathing. Her eyes finally softened with his, though her breathing still seemed unsure. Eventually, she filled in the gaps for him of what happened after he left the night previous.

His mind was spinning with uncertainty. "So he really broke up with you."

Jess couldn't believe it. After all the threats, all the scowls, Dean was giving up just like that? _I have a feeling this isn't over_ , he thought begrudgingly. Looking over at Rory, it was apparent she didn't think so either.

Rory looked up, gazing out at the lake. There was a fresh determination in her bloodshot eyes as she regained control of her body. "I think I have a plan," she said, somewhat steady. She licked her lips. "To get him back."

He wasn't completely surprised to hear that. This was the master of lists and organization, after all. "You want someone back who breaks up with you for studying with a friend?" he found himself asking. He had to challenge her. He wanted to test her.

"Well, I love him and he's nice to me and we've been together a long time," she shrugged. Catching the emotionless look on Jess's face, she quickly went on. "I mean, _obviously_ there's other reasons I want him back too. I don't know, I'm just confused. I didn't expect him to do that."

He gave a nod. "You _are_ a big fan of constants."

"Seems the universe is testing all of them lately," she sighed irritatedly. "The goal was always Harvard, and now I've let my grandparents talk me into applying to Yale too and a few other schools and my mom is all mad at _them_ about that, and mad at _me_ for going along with it. Then the workload at Chilton was hard for me at first so I had to have _you_ tutor me because I got a freaking D."

"Hey," his voice was soft. "We went over that before. Everybody gets D's sometimes."

"Still, that was hard. And now _Dean._ We've been together for forever." She picked at her nails nervously. "And… I mean, I don't know if we'll stay together forever or not. But right now I just… I need something to be stable." A couple hot tears blinked out of her eyes as she timidly looked over at him. "You know?"

His heart twisted. He knew. While his life had never boasted of stability, the times he had something resembling it had been good. Having a life like Rory's where things were less likely to make drastic steps like this had to feel jarring when it did.

He chewed the inside of his cheek. "Okay, I'll bite. What's this plan of yours?"

She inhaled sharply, looking away from him. Red dotted her cheeks. "Don't laugh."

"This is off to a good start."

"I'm serious!" She turned back to him, eyes wide and a small playful smile. Her features felt alive again, if only briefly.

He sighed. "Alright. I won't laugh."

Rory paused for a long time, obviously working up the courage. What she ended up saying threw him off completely. "Will you pretend to date me?" she squeaked.

"Excuse me, what?" He stared at her incredulously. "Pretend to _date_ you?"

"Yes."

" _Why_?"

"Because it will work."

"I doubt that."

Rory got to her feet and began pacing, transitioning into her planning mode. "See, that's what my mom said, but that's where I know you are both very, very wrong. Dean's big problem over the last several months has been you."

"Right," he inserted cautiously to show he was following so far.

"And he flat out told me he thinks I like you and obviously want to date you," she continued.

Jess felt a smirk rise up.

"But that's stupid." She shook her head. "I don't know where he's getting that. And saying all those things about _looks_ I give you. I don't give you _any_ looks. I just _look_ at you. Normally. Like I look at anyone else. It's just a _look_."

He was eager to stop her rambling, but stayed silent.

"So if we pretend to date and show him I'm dating you he'll realize he basically _pushed_ the idea of you on me and I had to go to you for comfort as a friend and then we started dating because I felt alone and lost without him! He'll see it was a misunderstanding."

"He'll see he misunderstood thinking you were interested in me when he sees us going out together," Jess said slowly, hoping she would start to see that it didn't exactly add up.

She rolled her eyes at him. "Ugh, you don't get it either. It makes sense, trust me. You and mom are just looking at it weirdly. I know Dean, and he'll realize he gave me no choice. He drove me to you!"

"Doing wonders for my natural charm here." He got up slowly and stared at her for a long time. "You honestly want to do all that just to date him again?"

She nodded. "I worked it out and it just makes the most sense. Things were going well and I just need to get everything back on track. I'll get into Harvard, mom will be happy again, and Dean and I will be together."

He pressed. "This isn't _only_ about stability, right? You honest, one hundred percent are over the moon for Dean and want him back?"

Rory swallowed and licked her lips before nodding. "Yes," she said with finality. "So… will you do it?"

"Huh?"

"Pretend to be my boyfriend to make him jealous."

He snorted. "Oh." He had already kind of pushed that thought aside, thinking there was something deeper there. But her eyes were sure and sincere, so it seemed there wasn't something more to this plan of hers. It really was about getting Dean back. He ran a hand through his dark hair and exhaled slowly. "You don't think it'll be awkward?"

"For Dean?"

"For us. We're friends, right now we're able to be openly friends without any boyfriends running in to yell at me."

She shook her head. "I have that worked out too. Once Dean realizes he still cares about me and I obviously care for him, I'll explain you and I definitely are only friends and he will have to accept it."

"And you think this time he will."

"He will."

"Alright, well back to the awkward for _us_ part. He'll have to see us kiss."

"Obviously."

"And it's going to have to look like we've become quite skilled at kissing each other."

She paused a bit. "Well, yeah. I mean, you can't look like you're hating it or anything."

He chuckled. "What I'm saying is, we should probably – I don't know – do some kind of official 'first kiss', get the awkwardness out."

She nodded enthusiastically. "Yes, that's perfect!"

"Wow, Ror, had I known you've been eagerly waiting to kiss me this whole time..."

"Shut up," she laughed, walking closer to him. "So, um, should we try that now?"

He shrugged. "We could."

She stared at him. "You really don't mind doing this for me?" she asked. "I mean, you aren't really getting anything out of it in the end."

"Suppose not," he said, "But surely getting to kiss you in front of him and get him worked up will be fun."

She laughed again before giving him a stern smile. "Okay, let's do this."

"Such a romantic."

"Well, it doesn't have to be romantic!" she argued, waving her arms.

"Don't you need a good story to tell people to make it convincing?"

She stopped and thought on it. "Actually, that's not bad, Jess," she grinned. "So, I'm guessing you have something here to start off the story."

"Well, you seem to think I have some kind of talent for writing so surely I must."

"I'm listening."

His heart pounded as he began to take it more seriously, thinking what he had wanted to say to her before, things he had gone over in his mind for nights but never liking how honest and open it was. He didn't share those kinds of deep thoughts. Doing it now will only make her think he's helping, so there wasn't much risk, right?

He took a step toward her, closing the small distance. "Well," he began. "You came over after Dean broke up with you and cried." His voice was soft. "I held you while you cried and you told me you'd never love anyone like you loved Dean and nobody would ever be able to treat you as well. So then, I tucked your hair back like this -" He gently smoothed back a strand of her, watching her stare up at him as she listened quietly. "- And I told you Dean was an idiot and if he truly wanted you to be happy he wouldn't have left you. I told you -" He paused, feeling his voice getting braver, "-You were the most gorgeous and intelligent person I've ever met and that I wanted to take care of you until Dean realizes his mistake, or until I can make you fall in love with me back."

Rory was blushing, he mouth slightly open as she registered his words. "That almost makes you sound better than Dean," she jested, but she remained focused on him and waited for him to go on.

Jess reached up and stroked her jawline, like he had started to the day before she left at the beginning of summer. He pulled her face closer, whispering, "And then, I kissed you," as he placed his lips on hers and drank her in.

It was a slow and building kiss. They had kissed for the play, certainly, but it was quick, and the unexpected jolt – that he at least had felt – had taken by surprise. But this was deeper. He was getting to know her rhythm, her feel – getting to know the things about kissing her he would need to know to make this game convincing.

In the back of his head he told himself he was an idiot and only going to crush himself by helping her do this. A small part of him _did_ believe maybe there was a chance she would fall for him and forget Dean in the process. There was a lot of history with Dean to compete with though. In the end, they would get back together. _But at least I can look back on this moment_ , he thought, as he deepened the kiss.

When they finally pulled apart he was pleased to see a somewhat heavy-lidded expression on Rory's face. She seemed to have to remind herself to breathe in, as there was a bit of a tremble to the small sound she made as she did so. Her eyes were shining when she finally opened them.

"Does that story work for you?" He asked her quietly.

She nodded slowly. "That… works for me."

* * *

 **A/N: Alright, so this is where the story is going now. I apologize if some of you aren't fans of fake dating stories, but I'm really into them for reasons even I'm not sure of haha. Call it a guilty pleasure.**


	15. Chapter 15

Rory had once mocked him for a 'dopey grin' she caught him making.

Whatever she would label the constant expression on his face as of late, he didn't know. She hadn't seemed to notice; her focus was too heavy on prowling around for Dean, or on her college applications, or the school paper, or her vice-presidency, or…

He grew dizzy thinking of all the things distracting her on a daily basis.

It was lucky for him though. Kept him from the teasing he would surely receive if she _had_ noticed his face. He found it a struggle to maintain his usual mask of indifference. The fact he now had permission to hold Rory's hand and kiss her lips was too damn satisfying to keep bottled up inside.

They did their Dean-scouting missions twice a week, during times Rory was free and knew where to expect to see her ex. Jess would be talking about the latest book they were arguing about when she would suddenly reach out, pulling him by the collar as her mouth met his. His brain would shut off as he melted into a puddle of his own being every time - the dopey grin forming on his face - as she pulled away and eagerly looked to see if Dean had been nearby to notice. Jess would attempt to regain his composure, usually stumbling a bit at first.

It had only been a few weeks and not many Dean sightings had been had. Rory mentioned sport teams he was a part of, but with her schedule, there wasn't much time to swing by any of the games or practices. They usually settled for walking around town - cuddling, kissing, reading out in the open – inviting enough gossip that even if Dean wasn't around on one of their scheming days, he was sure to hear about it.

It wasn't until after her college applications were sent off that a bit of the weight on her shoulders lifted and she seemed to take notice of how distracted she had been. They were doing their Thursday Dean-hunt – luckily this time she was free when he would be having basketball practice outside at his school – and she suddenly spoke up in a soft, somewhat regretful voice.

"I'm sorry everything's been kind of about me lately," she began with a heavy sigh. Her fingers were interlocked with Jess's, her gaze on the ground as they walked toward the outdoor basketball courts.

Jess felt his mouth tighten. "With the Dean stuff?"

She nodded. "And… my general freakish need for my life to be a certain way. It just kind of hit me that… I've kind of neglected you."

He rolled his eyes at her choice of words. "I'm not a puppy, Ror."

"I know, but I just made everything about me, totally not bothering to see how you've been!" She gave him her full attention, eyes big and shining. "How _have_ you been?"

"Um… fine, I guess." He gave a casual shrug. "It's not a big deal. It's been nice spending time with you. I wish it was a little _less_ about Dean, sure. I find rocks have more substance than _him_."

She ignored the slight. "Well, tell you what. Let's do something this weekend." She swung their arms merrily, a smile growing as she did. "You and me. No Dean talk. Back to bantering and arguing and having long-winded discussions! Deal?"

He liked the sound of that so far. "I could finally take you to that book shop in Philly."

Her eyes grew. "Oh my god, I forgot about that place. Yes, let's do that!" She bounced around. "I've never been to Philadelphia! I'll buy you a cheesesteak to apologize for being so crappy."

He scowled. "Ew, I'm not going to eat a cheesesteak. That's such a tourist thing to do."

"Why? We _have_ to! It's Philly! _The Big… The Big Steak_!"

"I think it's called _The City of Brotherly Love_."

She paused. " _The_ … _City of Brotherly Love One Has For Cheesesteaks_."

A small chuckle came out of him. "You can get one. I'll observe." This was starting to feel more normal. It seemed like forever since they had been like this – egging each other on, barely able to contain how much they both enjoyed the company.

"I can't just get _one_ ," she complained, rolling her eyes with a huff. "The place is known for them. I have to learn who has the best one."

He grinned. "Fine, fine. We'll get a cheesesteak."

"Cheese _steaks,_ " she corrected.

"Well, you better bring your wallet," he teased, eyes narrowing at her, "Fake boyfriends don't have to pay for their fake girlfriend's weird eating habits."

And he was cut off before he could continue. She was crushing herself into him suddenly, her arms wrapping around his neck, their chests and mouths colliding. The warmth of her engulfed him, the only heat he felt in the growing November chill surrounding them.

He stumbled back a bit from the surprise of her embrace and her kiss, but he steadied them quickly. He pulled her against him, hungry for more of her body heat - of her proximity. His mouth ravenously matched the pace of hers. A soft sound came up from her throat as she tangled her fingers in his messy hair. She pulled back after a minute, but kept her hands in his hair. Absentmindedly, she twirled a strand of it between her fingers as she met his hard gaze. Her cheeks were still flushed with heat.

"It turn you on to pay for yourself?" he quipped.

She kept her voice low, expression blank. "Dean's behind us. On the court. Stay still."

He felt the immediate pang he always felt when Dean got brought up in the middle of a great moment. Cautiously, he flitted his eyes over to the set of outdoor basketball courts a few yards away.

"Is he looking?" Rory asked.

Dean _was_ in fact looking. It was hard to make out his expression from the distance, but he definitely was looking.

"He is," Jess said quietly. He looked back at her. "Want me to do something?"

She frowned, curious. "Do something?"

"Well, it probably looks like we're having a moment over here," he continued, nonchalant. "He'd never be able to tell we were just talking about cheesesteaks, especially if-" He gently held her chin and brought her back to his lips. It was a gentle kiss that started with her mouth, then he trailed light kisses down her jaw. Fighting to pull away for a moment, he finished his thought in a dark, breathy voice. "-especially if I'm doing something like this."

 _You're an idiot_ , he scolded himself. _This is too much. You're driving yourself insane._ He felt the fire building inside him and he couldn't stop just yet. These were the only chances he had to flirt with her now. Judging by the soft, low whimpering she was making – and trying her best to hide – it was definitely a bit of a struggle for her as well as he continued to slowly kiss along her jawline.

"So, how many?" he said huskily, kissing hard against the spot below her jaw and ear. His eyes held where Dean was standing with his teammates in the distance. Part of Jess felt more aroused to be kissing Rory like this in public, where her ex had a clear view.

"Hmm?" she could barely get out, paralyzed by what was happening.

"… _Cheesesteaks_ do we have to locate for this contest of yours." His voice sounded so carnal. He had never heard himself like this before. _She's insatiable, and she isn't even doing anything. It's going to be impossible to break away from her. I want to live in this moment forever._

She exhaled, as if she had been holding her breath this whole time. "Um… m-maybe five. Or six. Or..."

He gave one last kiss to that spot he had been teasing before leaning back, fingers still gently cupping around her chin. Her eyes fluttered open, rolling back into place. "Is he still looking?" she asked softly.

Jess checked. "No."

She twisted up her mouth and gave him a slight shove. " _Dammit_ ," she hissed, and he knew it wasn't at the fact Dean wasn't watching. "You do these things to get me worked up and embarrassed on purpose!"

He grinned, unable to help himself. "Isn't this what you asked me to do?"

"N-not like _that_!" she exclaimed, eyes wide. "That was _way_ too much!"

He shrugged. "Dean's not going to believe _just_ you lunging at me like an attack dog. He's got to see some variety. 'Spice of life' and all."

She reddened angrily. "I… I don't _lunge_ like an attack dog!"

"You're pretty lunge-y." He leaned closer, cocking a brow. "Getting you _worked up_ , huh?"

She reddened more. "Not like _that_ , I mean _embarrassed_!"

"You _said_ embarrassed though. Worked up _and_ embarrassed."

Her mouth closed. She was caught. "Right..."

"So you're trying to tell me you were saying I'm getting you all embarrassed and… embarrassed," he stated, making a show of thinking it over. "Not worked up ' _like that_ '."

"I'm not buying your cheesesteaks now." She stomped off.

He jogged up to her with a laugh in his throat, grabbing her hand. She looked down at it horrified, starting to pull away. He gripped a bit tighter. "Ah, ah," he warned in a light tone. "What if Dean starts looking again? And if we're going back to talking about cheesesteaks," his tone grew playful, "I can go back to-"

She rolled her eyes and snorted, accepting his hand but kept her fast pace. "Who knew having a fake boyfriend would be this annoying. Come on, I need to get back and do homework."

They walked in silence back toward her house where his car was parked. Once they were out of sight of any townsfolk, Rory let go of his hand and folded her arms across her chest. Sad to lose the warmth of her touch, he shoved his hands in his pockets. They rounded the corner, turning onto her street.

He had still been musing over what had happened – finding it the perfect mix of enjoying her and teasing her - when it dawned on him just how upset she was. Her face was knit up in a tight bunch and she didn't look anywhere near his general direction. Each step she made was deliberate and echoed her vexation.

"Hey, I didn't mean to embarrass you," he said apologetically, playfulness dropping. She was too visibly upset to keep up his devilishness. "I got carried away. You know I just like teasing you is all."

She shook her head, jaw still squared. "Sometimes it's a little too _much_. The teasing. You _do_ all these things, _say_ all these things – just _stop_!" Her eyes were icy and furious. "I don't know how to handle it sometimes!"

"Look, I'm just trying to do what you asked," he snapped, eyes narrowing.

"Well, I never asked you to kiss me like _that_!" she shot back.

"Like _what_?"

"You _know_!"

"It's not _my_ fault if you're enjoying it," he scoffed bitterly. She surely had to have accounted for possibly _liking_ kissing him, right? This, the girl who plotted out every day of her life? "I'm just trying to make it more convincing than your stupid _lunging_." Growling, he started walking ahead of her. _I didn't ask for any of this. I'm just doing her a damn favor._ "Whatever," he muttered loud enough for her to still hear. "All of this is a joke anyway."

He jerked his keys out of his pocket as he got closer to his car waiting in her driveway. Quickly trying to get a grip on the right key, he dropped them and cursed. Fumbling to scoop them off the ground, he was too late as Rory came up and blocked the car door from his reach. The length of her – however short it was – was positioned casually against the car, covering the handle. Her demeanor had cooled a bit, but the tension on her face was still there.

"You were trying to apologize," she said with a sigh. Her voice was straining to return to its usual sweetness. "I just… didn't expect things would be like that when we did this stuff. Dean and I didn't do a lot of PDA, so… that just felt really weird to me. Having so many people around while being kissed like that."

He felt himself go weak at her sudden vulnerability. "Just was trying to sell it. I forgot you aren't really like that."

"Like what?" Her brow shot up questioningly.

"You just said yourself, you don't do super passionate."

"I said _PDA_. I can _do_ passionate!" She hesitated. "Just… not with an audience."

"Isn't that the whole strategy of trying to get Dean back?" he prodded. "Making it seem like you've moved on to something better and making sure he notices?"

She sighed, burying her face in her hands in frustration. "I'm sorry. _Whatever._ I have a headache. I'll just see you at school tomorrow."

As she started to head toward her front door, he felt a heaviness in his chest. "Are we still going to Philly on Saturday?" He was almost afraid to ask.

She frowned, spinning around. "Yes. Why wouldn't we all of the sudden?"

He shrugged. "You seemed mad at me."

"No, I want to go," she said. Nervously, she picked at her nails. Her eyes still wouldn't meet his directly for more than a second. "I think… I think it'll be good for us to hang out normally. None of this weird, fake passion stuff and kissing and touching. Just… normal talking and..."

"Whatever?" he offered, catching on to her current filler word of choice.

As much as he loved the new freedom of holding and kissing her – despite the obvious double edge it had of also paining him inside – he knew she was right. They didn't have the same relationship as before. Things were complicated now. They were friends that were doing more, but not – in Rory's case at least – out of real want. It was business. They had to remind themselves of that if they wanted to remain friends. Though Jess wasn't so sure what he expected from all this in the end anymore. He tried more often than not to ignore it.

He nodded finally. "Yeah. Okay. See you tomorrow."

* * *

He drove and insisted she have full control over the music.

She settled on a punk band she had been dying to get him into. After awhile, she pulled out a book and asked if he minded her reading aloud to him. He had flustered, somehow finding it intimate, and nodded in response. Her soft voice was enchanting as they continued their drive, a slight smile on his face as he listened. Their small spat just days before was forgotten.

They were back to how they were.

Rory had never been to a large city before, that much was clear as soon as they were parked and out on the sidewalk, taking in the sights and buildings. Jess couldn't help but laugh as she bounced everywhere with a checklist in hand, demanding to see historic landmarks - especially the Liberty Bell. They went there first, since it was the closest thing to them on her list. She kept trying to inch close enough to touch the bell, but in the end was too nervous she'd be caught and thrown in jail – ending her chance at Harvard before it ever began. He ducked into a gift shop and got her a small toy of it that was realistic enough to give her that sense of mischief minus the jail time. It wasn't the kind of thing he would normally do; he usually would call the gesture stupid and idiotic. But it was Rory and it was, after all, their day to be happy and enjoy each other's company. She made a big deal out of the gesture and he quickly grew red and dismissive.

Around lunch time, they began their circuit of cheesesteak shops. She had spent the night before thoroughly researching the best ones to go to, what they were most known for, and ratio of cheese to steak – something her mother had insisted she put as part of the judging criteria. It took over an hour to track down every place and order two of everything on Rory's list. Bags full of sandwiches and chips and drinks clasped in her hands, she was led by Jess's steady hand on the small of her back toward a park that did historic retellings in the afternoons. Spreading out a blanket she brought along, they cozied up away from the crowd, but close enough to still watch and hear.

Rory passed out the food and a couple sodas, before beginning her conquest. It was more food than Jess would ever eat in one sitting, but he found himself laughing at the speed at which she downed her food. She made faces of savoring and considering the flavors, jotting down notes in a small journal opened up beside her, and then moved on to the next sandwich. She always spoke of being a journalist, but he was beginning to think food critic seemed up her alley just as well.

After all her food was polished off – he was eating at a remarkably slower pace and _far_ less food - they sat back to enjoy the rest of the play. She leaned against him, subconsciously looking for extra warmth in the late fall air. Dropping the remains of sandwich on its wrapper, he wrapped an arm around her shoulder, tugging her closer. Her head leaned into the crook of his neck out of instinct and they hid small smiles from each other as they quietly enjoyed the show. When it ended and everyone applauded the actors, Rory soberly noticing her position. Jess waited for her to bolt up, fly off somewhere with him scurrying to chase her in efforts to calm her down. But she stayed. She looked up at him, still pressed against his side, and smiled before darting her gaze down. His heart skipped and he swore there was a blush on her cheeks.

They eventually made it to the bookstore and by the sharp intake of breath she made, Jess could tell Rory was happy they saved the best for last. Her eyes sparkled as she ran through the arches of books when they walked in and they widened further when she got to the main hub of the building. Jess followed her wordlessly, watching her take it all in. She went down aisles and pulled out another list, one with books and albums on it. Merrily, she began hunting some of them down.

He walked off at one point to grab them each a coffee from the little cafe in the back corner. When he went looking for her, she was motioning at him from inside one of the private booths with headphones. She had found a new album by one of her favorite bands and wanted him to listen to some of it with her.

They stretched the headphones as wide as they would go, snuggled their heads together, and listened as they drank their coffees and read side by side.

* * *

When they left Philadelphia to start the drive home, it was already dark.

He hated driving so late, but they got caught up in their purchases at the shop and then Rory wanted to grab food again – he didn't know how she wasn't still stuffed from lunch – before they headed back.

Now in the car, coasting along the nearly empty highway, they were silent. It started out a comfortable one, with the radio on low volume. Halfway home, Jess sneaked a few glances her way and noticed an increasingly troubled look in her eyes. She was staring out the passenger side window, brows furrowed and jaw clenched. He wanted to ask her what had her in such a polarizing mood from earlier. All day she had been bubbly and talkative. The contrast now was unsettling. He chose not to ask, allowing her more time to her thoughts.

Eventually, she spoke in a ghost of a voice.

"It's selfish I'm asking you to do all this, isn't it _."_ It wasn't a question.

They had gone all day not once mentioning Dean. With the way she let Jess still touch her and get so near to her, he half wondered if she forgot all about Dean. Just two days before she pointed out they needed to spend time together without this fake dating scheme making things feel strained, but she had reached for his hand all day, leaned to snuggle next to him; he grew daring and caught himself planting a soft kiss on her head at one point. After doing it, he immediately backtracked and excused himself off somewhere to recover.

He inhaled sharply, his grip tightening a bit on the wheel as his eyes remained ahead of him _How do I approach this,_ he thought, mind racing for a response.

"You just… want your life to go back to how it was. I get it."

" _Do_ you get it?" she frowned, turning to stare at him. He glanced over, catching the urgency in her blue eyes. She chewed on her lip with worry. "Because I'm starting to think all of this is stupid."

"You _are_?"

"Yeah."

"What about Dean?"

She sighed loudly, slumping in the passenger seat. "I don't know. It's naive to think he'll let you and me be friends if we get back together. I don't know why I was so sure that would be okay. It's hard to be logical when your life feels out of your control and you just want to fight to keep it all the same."

"Well, if you love him then… I don't know." He lowered his voice, feeling his chest tighten. "Maybe it'll be easier that way, so you can have the relationship you want."

She glared at him. "Easier _what_ way _?_ To stop being friends with you, you mean? _No_. Not an option."

He tossed her a playful smirk. "Yeah? I mean that much?"

"Well, you're really important to me," she said quietly, a faint pink reaching her face. It was apparent even in the dark. "And… I don't want to be with someone who won't trust me to have friends. I mean, he acts like we were running around making out everywhere."

"Well not _before_ ," he noted with a sly smile, "But we kind of are _now_."

"Yeah," she said softly.

She seemed distracted again. Her gaze was back out the window, a fingernail caught between her teeth getting slowly withered away.

He hesitated. "Are you saying you want to stop?"

It eventually would have to stop, he knew that. But the extra time with her had been good and he felt himself a bit disappointed all that might be over. _I'm not ready to figure out where we go from here yet_ , he found himself thinking as the disappointment grew. _I'm too afraid to._

"I… I don't know," she said honestly. The defeat was thick in her voice. "I just feel confused. I thought he would try to get me back sooner. It's been a few weeks now. He's seen us. But… at the same time…" Rory gave him a sidelong glance. "It's been great seeing you so much, fake boyfriend stuff aside."

"Huh. So my master plan to make you fall in love with me worked." He said it with a chuckle and shot her a teasing expression that he knew wasn't meeting his eyes. _What's she trying to say?_ he wondered.

She blushed more, but for once didn't retreat into her shyness. "Did you _really_ want that to happen?"

He stilled. His eyes swept back to the road as he took a steady breath. _Of course I wanted that. You deserve way better than that idiot_. "Rory, I get you feel confused right now. Maybe you need some time to figure out if you want to get back with Dean or not."

"Yeah maybe." She leaned back against the seat, angling to face him. Her eyes had a sense of longing to them, a far off look he was hoping was more than just contemplation. "I just… you've been really understanding.," she admitted. "And you can discuss books with me. And today felt _kind of_ like a date – even though it wasn't, and… I think it's the best one I've ever had." She was rambling a bit. "And as far as kissing y-" She stopped abruptly, eyes large.

He grinned widely, shooting a glance at her. "I'm sorry, what was that last bit?"

"Nothing." She shrunk away, turning back toward the passenger window.

" _Kissing_ , I believe I heard?" He cupped a hand around an ear.

She growled. " _Nothing_!"

Jess gave a casual shrug, playing as if he were considering her words deeply. "I suppose you _do_ have reference now of what kissing me properly is like. Only makes sense you might have drawn some comparisons."

Her eyes flashed as she shot back toward him, annoyance in her face. "What do you want me to _say_? _Fine_! _Alright_! It's not _terrible_ to kiss you!"

"Not terrible, huh? So… it's good." He couldn't deny the bit of pride swelling within him.

She snorted, folding her arms across her chest. "I've had worse."

"So… Dean."

"Wh- there could be others!" she objected, gaping at him.

Jess shook his head, his mouth straining to reveal his satisfaction at her reveal. "Except Dean's your first boyfriend and I know for a _fact_ your first kiss. So. In conclusion, I'm better than Dean."

Her eyes rolled. "God, you're so smug about it."

"Hey, I'm just trying to enjoy my compliment," he defended with a laugh. "Guess this explains why you got so mad over how I was kissing you the other day." Looking over, he saw she cowering into a tiny ball, clearly mortified. His heart softened. "Hey. Rory." He called out gently.

She didn't budge.

Sighing, he guardedly said, "It's not terrible to kiss you either."

She peeked up part of her head, revealing only her bashful eyes. "Yeah?"

"Yeah."

"So," she asked timidly, uncurling herself a little. "We got a little too good at kissing each other. What does that mean?"

"It means you sound confused about Dean right now," he said carefully, his tone hardened. He didn't want to press his luck. He already had been flirting unabashedly most of the day. He glanced over, a small smile returning. "And hey, if you go back to him in the end, maybe some of this _not terrible_ kissing you've been learning can rub off on him."

"I'm never saying anything nice to you again," she groaned, tilting her head back to stare at the ceiling of the car. She seemed more content, the strain on her face lifted. Her eyelids fluttered heavily and he knew she was close to drifting off.

Softly and sleepily, she called out his name.

He stirred. "Yeah?"

"I had fun today. Probably for the first time in awhile." She leaned over, resting her head against him and closed her eyes. "I won't let Dean stop us from being friends after all this. I… don't want to lost you."

She yawned and fell asleep.


	16. Chapter 16

People didn't knock on his door.

Jess ignored it at first, but the knocks persisted and he eventually got up. He was supposed to be meeting Rory in an hour, but at _her_ house so it definitely wasn't her knocking. Swinging the door open, he saw a burly man in flannel shifting back and forth nervously. His mouth twisted in amusement to see a man obviously in his mid-to-late thirties sporting a backwards baseball hat.

 _This is a sorry excuse for a door to door salesman,_ he thought, getting his sharp tongue ready to chase this stranger off. " _Look_ , we don't-"

The man gaped at him, finally snapping out of his awkward fumbling. "Jess. It's you. You're _here_."

 _Where else would I be?_ Jess narrowed his eyes. "Who the hell are you?"

The man cleared his throat, back to a state of uneasiness. "Um, well." He took a deep breath and gazed cautiously at Jess. "I'm your uncle. Liz's brother. Luke."

 _Luke_. Jess remembered the name, but barely the face. A brief memory of being taken to a sports game – he couldn't recall which exactly – and eating hot dogs with this man came to mind. That had been over eleven years ago.

"Okay," Jess said finally, still hesitant. He started to close the door. "Liz isn't here."

Luke rolled his eyes. "Sounds about right."

Jess smirked. "Huh." _He really does know Liz then._ He stopped trying to inch the door shut.

His uncle stared at him for a long moment. "Mind if I come in for a sec?"

Reluctantly, Jess opened the door further, letting Luke walk past him. He wasn't exactly bursting with time before meeting with Rory, but he was curious what his uncle was doing here after years of radio silence. Jess went into the kitchen and retrieved two beers, popping off the caps and bringing them into the living room where his uncle was now seated on the couch.

Luke glared when his eyes caught the bottles. "You're only eighteen."

Jess huffed, already impatient to be in this situation. "Relax, I'm not off getting wasted every day. Just figured this whole thing – you _randomly_ showing up – is weird. So maybe we both need one."

His uncle still didn't seem on board with it, but took the beer anyway. Tilting his head back he took a long gulp, draining half the bottle. Luke placed the beer on the table and nervously glanced at Jess, who was now seated on the edge of the table.

Luke finally spoke. "Right. So, you're birthday was recently."

 _Is that really why he's here?_ Jess rolled his eyes. "You don't owe me a card or anything."

His uncle gave a grunt. "No, it's not that. You know your friend Nathan?"

Jess felt his body grow cold, the chill creeping through him as he recalled a period he _had_ been getting wasted every day in ill attempt to cope with losing his long-time friend. "He's dead. What's it matter?" His words were as icy as he felt inside. He averted his eyes, but then frowned and faced his uncle again. "Wait, how did _you_ know Nathan?

Luke looked down, rubbing his hands together. "He was an old fishing buddy of mine. We'd go a few times a year up to my cabin and fish."

"Great." Jess sipped his beer dismissively. "Glad we have a whole 'six degrees of Kevin Bacon' thing going on here." The conversation was already longer than he usually allowed with anyone. The fact it was starting to lean toward his personal life made him eager to cut it off even sooner.

His uncle was growing short on patience as well, it seemed. "Jess, just _listen_." He shook his head, muttering to himself. " _Dammit_ , you're as smarmy as he said you were."

Jess frowned. "You guys talked about me?"

Luke gave an awkward shrug. "Yeah. Well, I first met Nathan when helping you guys move into this house. We stayed in touch and went fishing a few times. Then he asked me once what Liz did that kept her away a lot. I guess I thought having a kid would calm her down, but I was wrong apparently."

Jess scoffed, giving his uncle a knowing look. "I've learned you can't ever expect things from Liz."

His uncle nodded, grabbing his beer. He fumbled with it, not sure if he wanted to take another sip. Idly, his fingers picked at the label, peeling the corners of it. "So, I asked Nathan if he wouldn't mind checking in on you from time to time, make sure you were doing okay, had enough to eat and all that. He said you were always reading and I knew he had a lot of books so you'd probably get along." He hesitantly glanced at Jess. "After awhile, he started bringing you up in conversation on his own. He really took to you."

Jess had never spoken to anyone about Nathan. Mr. Medina had known him, sure, but he had never discussed Nathan with him. He felt uneasy. "So Nathan started giving me books because of _you_?"

"The book thing was his choice." Luke's voice was sure; nothing in it gave Jess reason to doubt his words. "I just wanted him to check in on you. I never expected… I mean, when he came to me when you were eleven, asking if he'd be able to adopt you somehow -"

"Wait, stop." Jess felt sick as the uneasiness grew. "That's not true." _Adopt me? Yeah, right._

Now it was Luke's turn to scoff. "Oh yeah? How do _you_ know?"

Jess shrugged and took a sip of beer, getting up to face away from his uncle. He knew how this went by now. "I was just some kid he took pity on. Why the hell would he adopt me?"

"Jess, he really cared for you. Did you _really_ never see that?" Luke was shocked at his nephew's dismissal of the relationship. "Didn't you care about him, see him as like a father or something?"

"Kind of." Jess shifted, wishing he was somewhere else. This wasn't something he wanted to think about. "Think he was like a father or something, I mean. He just was _there_ and listened."

"And you think he just thought of you as a nuisance? No. That man _cared_ about you. He and I tried to track Liz and Jimmy down forever trying to get paperwork rolling, but Liz would refuse, saying she was a great mom and nobody understood the setup you both had."

Jess laughed mockingly at that. "Anyone who has to announce they're a great mom probably isn't one."

"Exactly." Luke shared a look of amusement with him before continuing. "So, that dream kind of died, but Nathan decided to just still fill that guardian role despite nothing being official. When he told me he was going to leave you all those books, I was so glad. I never expected him to leave you the house too, and then all that _money_ …"

Jess's mind was racing. This conversation was too much. An uncle reappearing out of nowhere who knew his mentor figure, a possible adoption, money… _Wait._

He frowned, spinning to face his uncle again. " _What_ money?"

"That's why I'm here," Luke said with a deep breath. He slowly got to his feet and for the first time, had a confident and certain look in his eye that contrasted the earlier nervousness and fumbling. "Look, he told me he _only_ made you promise to finish high school so I have no idea what you're doing next. College, or hell, maybe go off traveling for a bit. I did something similar after high school for about six months."

Jess stared at him. "You did?" He shouldn't be surprised. After all, his parents both were wanderers. Maybe it was just genetic to want to be somewhere else.

Luke nodded. "I needed to after my dad died. Really helped me out. I don't think I could've opened up the diner if I hadn't taken that time to sort myself out."

Jess paused. He thought of Rory's small town. The place they went to eat. The place that she had commented was the best around for a burger and he had wholeheartedly agreed after having one.

"Diner." He tasted the word, letting it settle. " _Luke's_ Diner? In Stars Hollow?"

His uncle's face lit up. "You know about it? Did Liz mention it?"

"I ate there awhile ago. I have a… friend who lives there. Actually am about to head that way."

Now it was Luke's turn to look stunned. "Huh." He gave a small chuckle. "I must've been out of town fishing or something. That's nuts. That close, yet so far away."

Jess nodded. He went and fetched Luke another beer after seeing him finish the rest of the first bottle. His uncle accepted it with a short nod and popped off the cap.

Jess watched him for a long moment before speaking again. "So the money." Money was always such an unsettling concept to him. "There's never been any money."

"Nathan left it to me so I could come talk to you and help you decide what to do with it when the time came," his uncle explained after a drink. "I figure you probably didn't think college was on the table up until now because of finances, so this might give you enough time to think over what you want to do."

"There's no _way_ he left me enough to go to college."

"Wanna bet?" Luke handed him a folded up piece of paper he pulled from his front pocket. Jess took it and unfolded it delicately. It was a bank statement. "It'll get you through most of it. Scholarships of course will help too. Nathan's been adding to it for awhile." The man's face reddened and he grew nervous again. "And… I had contributed to it a bit too. Not as much as him, but still. Not that it matters."

Jess removed his eyes from the paper, raising his brows in disbelief. "You did?" he asked, head still spinning. "But you don't even know me."

"You're still family," Luke insisted. "And… through Nathan I felt like I knew you. He would tell me how school was going for you, things you talked about… when you were skipping at your old school -" He glared as he said that last part. "So we both worked to get you an interview at that Chilton you're at now."

This was seriously too much. It had been over a year since Nathan had been alive, at least nine months since he last saw Liz, and now out of nowhere an uncle was here in front of him – giving him money for college, giving him history he hadn't known about. He felt dizzy and put his beer down, no longer interested in it.

His eyes were blazing with frustration. "So why _now_? Why haven't you tried showing up until now?"

Luke seemed to have been anticipating that question and some of the anger behind it. "Nathan said you were… a bit standoffish. That trying to get to know you had taken him a long time and he wasn't sure how quickly you'd adjust to someone else… especially after he would be gone." He swallowed a lump in his throat and looked at his nephew sadly. "I'm sorry I couldn't try harder for you, Jess. But I'd like to try harder now. I'm not a people person either really, and I'm usually working a lot, but I'd like to be someone you can go to. Now that Nathan's gone. You gotta have somebody to go to. Everyone does."

"Huh." Jess stared at the paper for a long time, not sure how his day had spiraled into this.

His heart hammered as he kept reading the account balance over and over. _College._ It had been a far off concept to him for so long. Sure, he was smart enough, but he didn't know what he wanted to do or how he would pay for it all or if he could sit still through another four years of schooling. _But I could take time to wander a bit and maybe figure that part out,_ he thought. It had never been possible before; his mind had been made up to treat it as something other people did.

Yet here it was. An option at last.

"Who's your friend?"

His dark eyes darted up. "Excuse me?"

"Your friend in Stars Hollow."

His mouth twisted. Jess wasn't really sure he wanted to talk about this. "Rory," he said with indecision.

Luke smiled warmly. His entire demeanor softened. "She's a good kid. Very smart. Bookish, like you."

Jess couldn't help but start to match the smile. "I know."

"Pretty too." Luke went on. A glint reached his eye. "And newly single I believe."

That was a step too far. Jess dropped the paper and started to head toward the front door. "Okay, I think uncle/nephew bonding time is over."

"Did you ever meet that boyfriend of hers?" Luke made no motion to follow after him. His gaze was steady. He seemed to have picked up on Jess's guard going up stronger than ever at the mention of Rory. When Jess remained tense and said nothing, Luke went on. "I wasn't really a fan. Glad they broke up. She's too good for him."

"Try telling _her_ that," Jess couldn't help but say.

Luke made a face. "What do you mean?"

Jess's hand had been on the knob of the door, waiting to twist it and shoo out his unexpected guest. His fingers dropped from the metal and he gave an exasperated sigh. "She's… she has this dumb plan to try to get him back."

"In a revenge way?" His uncle seemed more confused than ever.

"No." Jess shot him an irritated scowl. She wants to be with him again."

"You're _kidding_." Luke's tone said it all.

Jess gave a gentle tossing of his arms in the air. "I wish I was. She asked me to help her make him jealous so I go out to Stars Hollow a few times a week to walk around with her."

Luke's brain seemed to be piecing things together. "And kiss her?" Jess didn't react and that seemed to only confirm it for his uncle. "You know, I've only caught glances from the diner, but I've been wondering who this new boy was she kept bringing around and kissing so… _publicly_. Her and Dean certainly never kissed like that."

Jess couldn't stop the smile. He remembered not too long ago the 'not-a-date-but-best-date-she-ever-had' excursion he and Rory had and the slip of tongue she made at mentioning she didn't exactly hate kissing him.

"You like her."

He hadn't realized how lax he had been at holding his usual indifferent expression until he heard Luke's comment. His smile immediately retreated back to a thin line. It didn't matter. He had already made himself known.

Exhaling, he gave a slight shrug of indifference. "What's not to like?"

Luke cocked an eyebrow. "Don't you think this plan is a bit counterproductive?"

Jess shrugged again, looking away. "She's smart. She needs to figure out on her own change isn't bad and that Lurch isn't worth the stability she thinks he's worth having around for."

His uncle narrowed his eyes. "But what do _you_ get out of it?"

"Can't I just help a friend?" Jess worked his mouth in thought. "It's the only time I really get to spend with her outside of school. I'll take what I can get."

Luke caught on that Jess was clearly done with the topic. He stuffed his big hands deep into his jean pockets and rocked on the heels of his feet. "Well, you know, if you'll be around Stars Hollow a bit, you can always swing by the diner," the burly man remarked casually. He was back to being bashful. "Say hi or something. I'll make sure there's a burger with your name on it."

 _He's closing up the conversation,_ Jess realized. Just fifteen minutes before, he hadn't wanted this man inside the house or to be talking to him at all but over the course of their dialogue – despite the several topics he hadn't anticipated or wanted to have – he seemed to connect to his uncle somehow. Luke didn't push subjects harder than he needed to and seemed to be somewhat of a kindred spirit. Jess didn't expect any Hallmark moments any time soon, but for the first time in over a year, it felt almost like it had back when Nathan was around and talking to him and filling that tiny bit of a fatherly role that Jess allowed him to fill.

Still, Jess remained guarded as ever. It was instinct. His sharp eyes cautiously shot up to meet his uncle's. "You don't have to do me any favors because I'm on my own, you know."

The man nodded. "Yeah. I know." Luke started toward the door, not waiting for Jess to say anything back. He curled his fingers around the knob and stood halfway out the door when he looked back at his nephew. "Just swing by sometime. I'd like to start making up for lost time." He licked his lips with uncertainty. "And… you know, Christmas is coming up. If you want to come by to have a warm meal, I'll be cooking for myself anyway. I can make whatever you like. Just… let me know. No pressure."

Jess nodded hesitantly. "Alright. Maybe."

Luke nodded back and shut the door behind him.

It felt like a mirror image right then of when Nathan first invited him over and Jess hadn't been sure if it was a good idea or not. In the end, though, Jess _had_ gone to Nathan's, the need to not be alone for just a tiny span of time too overwhelming at that age. Now that he was older and more used to the solitude, he wondered if he would find himself accepting the invitation.

* * *

 **A/N: I got asked if Luke was related to Jess in this world and... well, here's your answer!**

 **Thank you everyone for the patience. I'm in the middle of a move. I JUST found a place and am signing a lease this week and finally going to get settled! Hooray for no longer being homeless! I should be updating more frequently soon like I had been there for awhile.**

 **Thank you to everyone saying they are enjoying my writing style :) Again, first time writing in years and I've been having fun with it so it means a lot I'm bringing some enjoyment to others.**


	17. Chapter 17

"I'm sorry, you'll have to repeat that."

Jess rolled his eyes at Rory. He had been expecting her to give him a shocked reaction, but she was going a bit overboard.

He had left his house soon after his uncle had and was now in Stars Hollow with Rory, doing the second of their weekly rounds in the town square. Their round earlier in the week hadn't been successful. Dean had been nowhere to be found, and surprisingly, Jess noticed Rory hadn't seemed too bothered about it.

"I said," he started over, a bit annoyed to have so much attention placed on him, "That if I wanted to, I have a way to pay for college. At least some of it, if I can get scholarships for the rest. _If_ I decide to go. Rory, I need to make sure you're hearing the word _'if'_ here."

It was too late.

She was bouncing around, her sea-glass colored eyes a torrent of excitement. "College!" she cried out, clasping two gloved hands together. "See? Aren't you glad you applied!"

She embraced him tightly, giving a quick kiss before pulling back with a wide smile. There was something almost ethereal about seeing her so blissful as the snow fell around her, freckling itself across her heavy jacket. Blinking out of the daze, he realized what she had done so spontaneously.

His head swirled. "Did… you just see Dean somewhere?"

She gave him a curious look. "Huh? No." It took a second before her face changed to mild embarrassment. " _Oh_. Sorry! I guess it's becoming a bit of a habit. I didn't even think… I… sorry, I'm just so excited for you!"

He sighed as they continued walking. "Remember, _'if'_."

It was half flattering and half troubling she was lapsing in their fake relationship. He already had a hard time with how blurry the line was becoming. He didn't need her to blur it further.

"Okay, okay." She calmed herself, but shot another sly smile as she linked an arm with his. "But it's kind of cool, right? Just admit it."

He scoffed. "I'm not admitting anything."

"Oh, _come on_! Humor me, please!"

"I already did by doing all those stupid essays." A smirk crossed his lips. "Not to mention, I'm helping you terrorize your ex into getting back together with you. I think I'm humoring you plenty."

She reddened. They hadn't really discussed her wavering thoughts on getting back with her ex, but Jess was noticing her lack of enthusiasm about it lately. They still made their plans to 'stalk' him and she still spoke as if they would get back together, but her commitment was faltering. Her voice didn't hold the same confidence it once had.

 _And now she's slipping up and kissing me when he isn't around_. He wasn't necessarily against these developments but he didn't know what they meant and wasn't about to start reading more into them than he should be.

Noticing her silence, he gave a lighthearted shove against her. "Though there's worse things I could be doing than kissing you to bug some guy."

She peered at him with interest. "Like what?"

"Listening to you bully me into going to some preppy college for one."

Her eyes grew. "It's not _bullying_ , it's _support_!"

"It's not lost on me you are literate enough to mask and repackage anything to sound nicer, Rory Gilmore," he remarked. His dark eyes stared into hers, filled with amusement. "Call it what you will, but this is an after school special and I'm being peer pressured."

She made a show of rolling her eyes, groaning at his playfulness. "You're such a drama queen. You should try out for theater." Waiting a beat, she flashed him a mischievous smile. "When you get to _college_."

Scoffing, he gave her another flirty bump to the side. "At least your weird scheme is good for one thing. Guess I'll be around to get to know this long lost uncle of mine."

She shook her head in disbelief as they passed the diner in question. "That's so crazy. Luke is almost like a dad to me. He's always helped me and my mom out when things have been hard. Not to mention, we pretty much _live_ at that diner. You said you hadn't seen him in over eleven years?"

It had slowly grown darker as they had been walking and the diner was the closest source of illumination to them. Naturally, Rory watched her townsfolk chatter away inside. Jess, feeling nervous, didn't look in just yet.

He nodded. "Him and Liz didn't see eye to eye. She thought he was always belittling her for all the drinking and drugs and what not, so basically made him stop coming around."

"So he sent Nathan to be around instead." Rory frowned in thought. "But if your parents aren't home that much, why couldn't Luke just do it himself?"

Jess twisted his mouth into a grimace. "Back then, they bothered stopping in more often than now. It would at least be once or twice a week. So Luke had no way of knowing when it started turning into once or twice a month and eventually just a few times a year. If Nathan ever came by and Liz was home, he had the excuse he was out walking his dog. Estranged brothers who don't approve of your junkie habits don't get that luxury."

Rory nodded. She gave a gentle squeeze to his arm. "Well, that's sweet of him to have gotten someone else to watch out for you. I know Luke and he has a big heart. I'm sure he wanted to do more." She chewed her lip in thought. "So, he invited you over for Christmas. Are you going?"

Jess caught himself glancing inside, watching his newly rediscovered uncle scrubbing away at the counter. The diner was bustling, most likely due to the extreme cold outside. He felt a small smirk cross his mouth as he gave another quick look to Luke, who was giving a scowl to a woman sitting at the counter, thrusting an empty coffee cup at him.

"I don't know yet," he finally said. "But he seems alright."

Rory smiled, following his line of sight. "I hope you decide to go. You're both two of my favorite people. It's nice to know you're related and can maybe be a real family together this time."

He reddened a little at the compliment, but didn't say anything.

They ducked into the rental store so Rory could pick out a movie to watch with her mother later that night. He followed her as she weaved through the aisles, looking for something that would be fun to ridicule. She stopped in the sci-fi section and began scanning titles quickly. Jess grabbed something with a strange cover and turned it over to read the back.

He heard the bell on the door go off and unconsciously looked up. His stomach heaved at the sight of Dean ducking inside. This was the closest encounter they had had with him so far. Glancing to Rory, Jess noticed she wasn't on her usual guard.

"Dean spotting," he whispered.

She looked up with confusion at him, then glanced over to where he was motioning. Her eyes took a moment to register her ex's presence and she slowly moved closer to Jess. _That was weird. Usually she's the one to notice him first._

Dean scanned the displays, looking for a certain genre marker and his gaze fell to them. He didn't look mad exactly; indifferent rather. _Isn't that_ my _schtick?_ Jess thought. Dean started to move toward them, with heavy and reluctant steps. _Obviously trying to be the bigger person all of the sudden by talking to us._

The indifferent face made a bit more sense as a tall blonde haired girl followed behind him, her fingers locked with his. Jess gave a quick glance to read Rory's face. She was caught off guard, that was obvious. Her face was always so doe-eyed; it made perfect sense she could pull off ' _deer in the headlights_ ' to the letter. Instinctively, he reached out for her small hand to show he was still there. She shot him a grateful look before turning back to the approaching couple.

"Rory, hey." Dean spoke as if he were pulling teeth.

Rory faltered a bit. "Hey." She didn't seem upset, but she didn't seem at ease either.

"Rory!" The blonde opened up her arms and embraced her. "It's been forever! How's your new school?"

Rory gave her reserved smile Jess usually saw her give Dean. "It's great, Lindsay. Just waiting to get those college acceptance letters in. Chilton really helped me prepare for it all."

"Lindsay and I have been kind of seeing each other," Dean mentioned.

Jess felt himself snickering inside. _What, don't want to claim this one as '_ your' _girlfriend? Have you changed your possessive nature that quickly?_

"Oh, t-that's great! Good!" Rory wasn't her usual prepared self. "Um, yeah, Jess and I kind of are too."

"Yeah. I've seen you guys around town a few times." The voice was cold.

 _Well, that answers if he's noticed or not,_ Jess thought, _And he seems to mind. So I guess Rory wasn't completely cracked when she said this would work._

Lindsay ended up excusing herself to look for a particular movie, leaving the awkward triangle alone. Jess knew it was the first time Dean had approached Rory since the breakup. _She probably wants me to leave so she can talk to him alone._ He excused himself for a cigarette before Rory could say anything one way or the other and left.

Sitting on a bench across from the store so he could look in, Jess puffed angrily on his cigarette. He hated this. He really didn't understand why he had accepted doing it. Every time he started to get lost in just being around her, then something brought him back to reality. The fact Rory was finally getting to talk to Dean face to face had to mean progress.

"Can I share?"

Jess looked up and noticed Shane standing in front of him, smirking. Despite the freezing temperature, her jacket was unzipped, her loose shirt falling open as she leaned forward to put her face just inches from his. She pushed back some of her short bleached hair and sat next to him. He extended the cigarette over to her. She accepted, taking a long drag as she watched him carefully. He knew she lived in the town, but hadn't seen her since the summer.

"Strange to see you here so much these days," she remarked, leaning back.

 _But apparently she's seen me,_ he observed. He took his cigarette from her and inhaled it. "Yeah. Weird town you got here."

Her smile was faint. She stretched out her legs, kicking at the snow with her boots as she did. "Seems things with you and America's sweetheart worked out okay."

He scoffed. "Yeah, right."

Shane raised a brow. "Pretty sure I've seen you guys go at it a few times."

"That's just cuz she's trying to make Frankenstein's monster jealous." He waved over at the video store. Shane dragged her gaze over and saw the former couple in a deep conversation together. Both were smiling and appeared to even be sharing a laugh.

"Seems it might be working," Shane muttered. Her eyes went back to Jess. "So what are _you_ getting out of it, getting to dirty up a sweet small-town girl?"

He grunted. A lot of people suddenly seemed interested in 'what he was getting out of it'. "She's a friend. I'm helping her out."

"You don't think this is super 'high school' and stupid?" Shane smirked in disbelief. "Hell, I'm surprised _she_ even thinks it's going to work. She's supposedly this _brainiac_. Didn't she get into that fancy school you go to?"

"She's pretty naive about dating. It's her life. She'll figure it out."

"Doesn't it suck though?" Shane gestured at the ex couple, though Jess's gaze was still firmly on them. "You _obviously_ are into her. Doesn't it suck getting to kiss her knowing she's thinking about _him_?"

Jess didn't like how easily she seemed to be picking through his brain. "I just don't think about it."

Shane leaned close again. "I think you do."

He shot her a dark look. "I think you just want me to think about _you_."

She shrugged. "Maybe. But it's whatever to me. I know you'll go off and do whatever once you graduate. Why get hung up over someone who won't be around?"

"Seem pretty hung up now." He sucked hard on the last bit of cigarette.

"Or maybe I just want you to know I'm still around if you get bored." Her tone was confident, her gaze steady and hungry as it met his. "I'm not an idiot. That girl isn't letting you do more than kiss her to get back at that guy. Kissing is fun and all, but those feelings build up. I'm just saying, I'm around if you need to… release those feelings."

He studied her face for a moment as she bore into him lustfully.

"Maybe," he said, noncommittal, taking a final inhale of smoke.

He wasn't sure if it was annoyance at Rory or just an excuse to push her out of his mind for a second, but he found himself leaning over to kiss Shane. She tasted smokey, like he was sure he did, but mixed with traces of bubble gum. The kiss felt good. Nice. But it wasn't the electricity he was used to. _I'm comparing her again to something that isn't real. This is just how things are. Not everything is electric._

He pushed away, feeling sick.

"Not here," he muttered, staring away from her. His mind raced for an excuse to give. "Still trying to be a fake boyfriend."

Maybe he would call her, maybe he wouldn't. The option was there now, if he needed to escape that badly. _This day keeps getting more and more surreal._ First Luke and the money, and then Dean and Rory talking. And now Shane was doing her own part to mess with things.

Shane cocked an eyebrow with a smoldering look still on her face as she got up. "You know how to find me."

As she walked away, he shook his head and cursed. She was right. He had definitely been a bit built up over the constant tease of getting a taste of being with Rory. It was torture. Maybe he needed someone else to take his mind off of it all. Maybe he needed to tell Rory he was done doing all of this.

"Jess?"

He blinked, seeing Rory suddenly in front of him. She had a plastic bag wrapped around her wrist with a VHS tape nestled inside. Her face was unreadable, but studying him closely.

"Oh," he said simply. "Hey."

He tossed the remainder of his cigarette on the ground and they began walking. He started to reach for her hand, but Rory didn't respond to the movement.

She glanced at him from the corner of her eye. "Was that Shane?"

He nodded, settling for stuffing his hands in his pockets instead. He didn't have gloves and if she wasn't going to take his hand, he damn well wasn't going to leave them exposed to the cold for nothing. "She and I used to go to the same school. I'm honestly surprised she doesn't go to Stars Hollow High. It's way closer."

Rory nodded as she listened, twirling the bag around to keep herself occupied. "Did you guys… used to date or something?"

He hesitated. "We hung out a bit during the summer." _By hang out, I mean I flipped out on her the second you called, kicked her out, and I haven't seen her since._

Rory's demeanor grew a bit hollow. "Guess I didn't know you knew each other."

"You might've had you bothered to contact me back then," he spat.

It was out before he realized it. He didn't know he still felt angry over it. He didn't _think_ he was. But Rory was speaking with Dean again and Shane had been prodding him and he suddenly had an uncle reaching out and he just…

 _Fuck._ The look on Rory's face made him regret the outburst.

"I thought you had forgiven me." Her voice was angry and hurt.

He winced, shutting his eyes tightly. Softening his expression, he exhaled. "Sorry. I'm just… kind of in a mood right now. Long day."

"Did she say something to you?"

He rolled his eyes. "She said a lot of things. It doesn't matter." He raked his fingers through his hair, brushing out the snowflakes. "You have a nice chat with the ex?"

She idly played with her hands, avoiding his eyes. "It was alright."

That wasn't like her. Normally she was more chatty, gave more detail than necessary. _Nothing about her seems right today._ Jess chewed the inside of his cheek. "So no progress then?"

She shrugged, lost in whatever she was thinking about. "I don't know. Lindsay was there. I didn't know about Lindsay. He still seemed kind of jealous, though. Don't you think?"

 _I definitely saw a flash of that usually possessive face_ , he thought. "Maybe," was all he said. "Does that make you happy?"

"I guess it should, shouldn't it," she said quietly.

They walked in silence, admiring the snowfall as they neared Rory's house. She told him stories about how her and her mother loved snow and they always took walks together during the first snowfall of the season. He thought it sounded nice. It was something that seemed so natural for her to do. She eventually slipped her fingers into his, though they were well away from the prying eyes of the town. He didn't object.

"So this college thing," she said carefully after awhile, swinging their clasped hands gently. "Kind of interferes with your Kerouac plan, huh?"

"I wasn't going to do _On the Road_ to the letter," he muttered with a sigh. "Just a trip _like_ it." He rubbed his thumb in a circle on the back of her gloved hand. "And… _if_ I go to college, I could still do my trip. Just over the summer before instead."

She gave a light, approving smile. "That could work. Some people wait for college to discover themselves but leave it to Jess Mariano to go find himself _before_ college."

"Hey, in _Almost Famous_ , he was still a kid when he had his big life discovery trip."

She huffed, the wisp of breath dancing in front of her face. "Not _that_ movie again."

He stared at her, baffled. "What!"

"You have a serious problem with it." Her look was accusatory.

A grunt left his throat. "You're cracked. It's a good movie."

"It's not a bad movie, sure. But you treat it like it's the Bible of movies."

"That's a stretch."

"Is it?" They arrived at her porch and she grew somber. She shifted a bit, her fingers still meshed with his. "My mom will probably be back with our food and snacks soon. I better get inside." They released contact and started to part before she whirred back toward him. "Oh, wait. I have my next book for you. It's in my room. Come on."

She darted inside, leaving the door wide open. He gaped, not expecting her invitation. Carefully, he stepped inside and followed her back toward her bedroom. He had been inside her house before, but never in her room. It felt like an invasion somehow, like he was entering something he shouldn't be. She stared at him questioningly as he hesitated outside the door. Taking a breath, he stepped in.

It was exactly the kind of room he pictured for her. Calming. Minimal of trinkets. Filled with books. And as she promised, books pouring from more places than just the shelves. She was pulling out drawers and rifling through volumes before landing on a particularly thick book and placing it into his hands. He tested the weight of it, raising a brow at her.

"A lot bigger than the ones you usually give me," he commented.

She nodded, closing the drawer she had pulled it out of. "It's an old favorite. It was easy to just skim through and jot down thoughts I've had over the years about it. I couldn't even tell you how many times I've read it. Have _you_ read this one?"

It was always a contest for her. She loved asking if a book was new to him, because they rarely were. Her eyes would light up and wait for his answer, but fell a bit when he would say he had. This time his answer was different.

"Never," he remarked, turning it over to inspect the back. "Always heard good things, but never came across a copy or remembered to look I guess."

Her face was luminous. "Finally!" she cheered, giving a small fist pump to the air. "I've finally found a book you haven't read! This is truly a victorious day!"

"A frabjous one," he quipped, smirking at her.

She took the bait. "Callooh, callay!" Smiling, she grew serious again, her eyes still and piercing into his. "You honestly haven't read this one?"

He held up a hand as if giving a pledge. "Honest."

"Good." Her relief was audible. "You have no idea how hard it is to think of books I know well enough to add notes to that you haven't read yet."

A low chuckle escaped him. "You know I never mind reading something again."

"But it's a victory, like I said." She was determined she had won.

"Is it really that big of a deal?"

Her face was firm and certain. "It is."

"I'll start it tonight then," he promised, tucking the book under his arm. "I should go."

Rory waited a moment. She was absentmindedly playing with a strand of her hair, her eyes focused on the tip of it. Her voice seemed a bit apprehensive. "You could… stay."

His throat dried up. "Stay?"

She blushed and motioned toward the living room. "Stay and watch the movie with me and my mom. Pig out on junk food with us. Honestly, you'd enjoy the way we make fun of movies. Right up your alley."

He wasn't sure. Meeting Rory's mom was big; he knew that for a long time now. Lorelai was her best friend, and an avid supporter of Team Dean. He didn't even want to begin considering how awkward the situation would be, especially with Lorelai knowing the situation her daughter was currently in with him. His stomach tightened just imagining how it would go.

"I've got some things to do," he lied. "Maybe… next time."

Rory's face fell, her eyes rushing up to meet his. He hated seeing the disappointment in them. "Okay," she said softly. "I'm sure she'd like to meet you, so… I hope you'll stay next time."

He scoffed. "She wants to meet me? Thought you said she thinks your plan is dumb."

Rory gave a short laugh. "But she knows you think it's dumb too." She went back to playing with the strand of hair. "And that you're important to me and we talk about books and that you helped tutor me and… she just…. She knows you're important."

"I'm important," he repeated slowly.

She dropped the strand and stared at him. "Of course you are."

The tension in the air was thick. He needed to leave. Being here with her, in her room, with all these books – it felt too similar to the time he had her in his own library and how she just seemed so perfect and beautiful and right in that moment. She was staring at him so confidently after declaring his importance to her. He wanted to touch her – _really_ touch her, not just for some ruse.

"Sweets!" a loud voice called from the front door. "I have every kind of pizza under the sun as well as several kinds of chocolate! Did you know they make chocolate with apples in it? I obviously didn't buy it. Fruit can dress itself up all it wants, but it won't win _me_ over."

"Mom," Rory breathed softly as her mother continued rambling in the foyer.

He was aware of how close Rory was to him. Her eyelashes fluttered as she peeked up at him, her look one begging him not to go, but knowing he would regardless. _It's better if I don't stay. She's slipping up too much today._

Jess nodded. "I'll go out the window."

She made a face. "You don't have to do that."

He shrugged and beat his fingers against the book he was grasping. "I know. But I should. It's not the right time to meet her."

Rory seemed intrigued by that. "Right time?"

"There's certainly a better one than now." He tossed her his usual smirk.

Walking over to her window, she thrust it open, the cool air beating against both of their faces. She turned to him with flushed cheeks and his heart hammered wildly. He climbed halfway through it and turned back to her to murmur a goodbye. Before he could, she was inches from his face and was knotting a thick scarf around his neck. His breath caught in his throat as he watched her face while her fingers worked around him.

"You really need to wear more than just a leather jacket when we go out walking," she commented, tucking the ends of the scarf into his coat. She delicately zipped it up as far as it would go with the new article of clothing inside and pulled her gaze up to meet his. Rory leaned closer, eyes glowing.

"Stay warm, Jess."

He felt his smirk grow. "I will now."

* * *

 **A/N: Thanks everyone for the understanding about the moving situation! First night in my new house complete! :)**


End file.
